Nitrogen Bonded To Carbon Of Organic Radical (e.g., Amino Acids, Etc.) Patents (Class 562/553)
  • Patent number: 4329297
    Abstract: A process for continuous or batch preparation of an .omega.-amino-acid is scribed, comprising the imination of an unsaturated aldehyde acid, the catalytic reduction in a single hydrogenation step of the imine of the ethylenically unsaturated straight chain .omega.-aldehyde acid in the presence of ammonia and an alkaline metal hydroxide whereby the alkaline salt of the imine is obtained, and the acidification of the alkaline salt of the .omega.-amino acid. The imine of formyl alkenoic acid is prepared at most at room temperature adding the acid to an ammonia solution of above 10%, then adding NaOH solution to the ammonia solution. The reductive imination is effectuated in two steps, first at 100.degree.-150.degree. C. and the second at 150.degree.-180.degree. C. under a 20-70 Ate pressure in the presence of a nickel catalyst. High yield and only few by-products are obtained.
    Type: Grant
    Filed: March 18, 1980
    Date of Patent: May 11, 1982
    Assignee: SNIA VISCOSA Societa' Nazionale Industria Applicazioni Viscosa S.p.A.
    Inventors: Pietro P. Rossi, Mario De Gaetano
  • Patent number: 4324886
    Abstract: Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.
    Type: Grant
    Filed: May 6, 1980
    Date of Patent: April 13, 1982
    Assignee: Phillips Petroleum Company
    Inventors: James T. Edmonds, Jr., Lacey E. Scoggins
  • Patent number: 4322547
    Abstract: Process industrially and economically useful for preparing difunctional aliphatic organic compounds of formulaX-(CH.sub.2).sub.n -Yin which n=6,7, X=--COOH, --COOR, Y=--CN, --COOH, --CONH.sub.2, --CH.sub.2 --NH.sub.2 --COOR wherein R is a linear or branched alkyl containing 1-6 carbon atoms.The process starts from a ketone of the formula ##STR1## in which n=2,3 and R.sub.1 =--CN, --COOH. The ketone (I) is changed to the corresponding hydroperoxide by means of H.sub.2 O.sub.2, the hydroperoxide is catalytically split by means of a catalyst Fe.sup.++ /Cu.sup.++ to give an unsaturated acid of the formulaHOOC--(CH.sub.2).sub.3 --CH.dbd.CH--(CH.sub.2).sub.2 -R.sub.1and this is catalytically hydrogenated to the compoundHOOC--(CH.sub.2).sub.n -R.sub.1When R.sub.1 is different from Y, R.sub.1 is changed to Y through known methods.
    Type: Grant
    Filed: July 21, 1980
    Date of Patent: March 30, 1982
    Assignee: Brichima S.p.A.
    Inventors: Francesco Minisci, Paolo Maggioni, Attilio Citterio
  • Patent number: 4304942
    Abstract: A process is provided for producing substituted 2-cyclopentenones represented by the general formula: ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are hydrogen or lower aliphatic hydrocarbyl groups. The process comprises treating a nitroalkane with a substituted acrylic acid ester in the presence of a base, followed by saponification, to yield a substituted 4-nitropentanoic acid which acid is then treated with strong acid under dehydrative conditions to yield the subject 2-cyclopentenone.
    Type: Grant
    Filed: May 21, 1980
    Date of Patent: December 8, 1981
    Assignee: SCM Corporation
    Inventor: T. L. Ho
  • Patent number: 4302402
    Abstract: A novel process for the manufacture of oximinonitriles which comprises the reaction of an oximinohalide with cyanide ion.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: November 24, 1981
    Assignee: Zoecon Corporation
    Inventor: Jeffrey N. Labovitz
  • Patent number: 4297275
    Abstract: Mammalian collagenase is inhibited by compounds having the formula ##STR1## and salts thereof, wherein R.sub.1 is hydrogen or alkanoyl of 2 to 10 carbon atoms;R.sub.2 is hydroxy, amino, or ##STR2## R.sub.3 is hydrogen, alkyl of 1 to 4 carbon atoms, ##STR3## R.sub.4 is hydroxy, amino, arginine, leucine, glutamine, alanine or glycine; andm is 0 or an integer of 1 to 9.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: October 27, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Joseph E. Sundeen, Tamara Dejneka
  • Patent number: 4290972
    Abstract: 4-Amino-2-hydroxybutyric acid or 2,4-diaminobutyric acid may be readily produced by a new process comprising reacting a propionic acid compound containing a .beta.-carboxamido substituent (-CONH.sub.2) on the carbon atom at the 3-position and optionally containing hydroxyl substituent and protected or unprotected amino substituent on the .alpha.-carbon atom thereof, with an alkanoic acid anhydride in liquid pyridine to convert the carboxamido group into a nitrile group, with occasional acylation of a .alpha.-hydroxyl group, occasionally removing the alkanoyl group from the .alpha.-acyloxyl group of the resulting nitrile intermediate, and then reducing the resultant nitrile compound with hydrogen to convert the nitrile group into an aminomethyl group, and further optionally removing the residual amino-protecting group from the resultant 4-aminobutyric acid compound.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: September 22, 1981
    Assignee: Meiji Seika Kaisha, Ltd.
    Inventors: Toshio Yoneta, Seiji Shibahara, Shigeo Seki, Shunzo Fukatsu
  • Patent number: 4288592
    Abstract: There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
    Type: Grant
    Filed: April 30, 1979
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Michael M. Rauhut, Shin-Shyong Tseng
  • Patent number: 4273664
    Abstract: Rust-inhibiting compounds, especially for aqueous systems such as tool-lubricating emulsions for machine tools and which consist of amine salts of a number of monoaminoalkylene dicarboxylic acids are disclosed.These rust-inhibitors are used in combination with water and an alkanolamine.Examples and test results are given.
    Type: Grant
    Filed: May 22, 1979
    Date of Patent: June 16, 1981
    Assignee: Snamprogetti S.p.A.
    Inventor: Ernesto Brandolese
  • Patent number: 4271318
    Abstract: An .omega.-lactam having 4-12 carbon atoms, an oligomer thereof or a ring-opened polymer or an .omega.-amino carboxylic acid corresponding thereto, is heated in the presence of water and a metallic carbonate compound to obtain a metallic salt of .omega.-amino carboxylic acid. Barium, calcium and lithium are the preferred metals. The resulting metal salt is converted to an amino Schiff base which may be used as a starting material for preparing an .alpha.,.omega.-diamino alkane which may or may not include an amino group as a side chain. This further produces a metallic carbonate compound. The metallic carbonate is returned and used again as a reagent for forming the metal salt of the .omega.-amino carboxylic acid to create a closed system.
    Type: Grant
    Filed: September 28, 1979
    Date of Patent: June 2, 1981
    Assignee: Toray Industries, Inc.
    Inventors: Tsutomu Setsuda, Hideyuki Aizawa, Takeshi Kimura
  • Patent number: 4264771
    Abstract: Manufacture of 4-substituted oxazolinone-(5) compounds, which are intermediates for .alpha.-substituted aminoacids, by alkylation of 2-substituted or 3,4-disubstituted oxozolinone-(5) compounds in an aprotic solvent in the presence of a tertiary amine.
    Type: Grant
    Filed: March 29, 1978
    Date of Patent: April 28, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Steglich, Rudolf Hurnaus, Peter Gruber, Boerries Kuebel
  • Patent number: 4260820
    Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more ruthenium catalyst components and an iodide or bromide promoter.
    Type: Grant
    Filed: September 24, 1979
    Date of Patent: April 7, 1981
    Assignee: Texaco Development Corp.
    Inventor: John F. Knifton
  • Patent number: 4243678
    Abstract: Compounds of the formula ##STR1## wherein R is (a) optionally-substituted and optionally-hydrogenated biphenylyl, (b) optionally-substituted and optionally-hydrogenated bicyclic aryl having from 8 to 12 ring carbon atoms or (c) a radical of the formula ##STR2## R.sup.1 is aliphatic hydrocarbyl, alicyclic hydrocarbyl or optionally-substituted phenyl;R.sup.2 is --H or lower aliphatic hydrocarbyl;R.sup.3 is --H, lower alkyl, cycloalkyl, optionally-substituted phenyl or, with R.sup.4, alkylene;R.sup.4 is lower alkyl, cycloalkyl, optionally-substituted phenyl, optionally-(nuclearly)-substituted phenalkyl or, with R.sup.3, alkylene;or R.sup.2,R.sup.3 and R.sup.4, together with the carbon to which each is bound, are adamantyl; andn is 3, 4 or 5;and salts thereof with a base are pharmacologically active. Esters thereof are valuable intermediates for the preparation of the pharmacologically-active compounds. Physiologically-acceptable embodiments are administered, e.g.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: January 6, 1981
    Assignee: Byk Gulden Lomberg Chemische Fabrik GmbH
    Inventor: Walter Krastinat
  • Patent number: 4234744
    Abstract: Aminoacid hydrochlorides or diaminoacid dihydrochlorides are produced by first reacting a halocarboxylic acid ester with an alkali metal cyanate in the presence of an alcohol to form the corresponding mono- or diurethane and then saponifying this to the corresponding mono- or dihydrochloride. The new process is relatively versatile in its use and above all opens up an elegant synthesis route for lysine.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: November 18, 1980
    Assignee: Deutsche Gold- und Silber Scheideanstalt vormals Roessler
    Inventors: Franz Effenberger, Karlheinz Drauz
  • Patent number: 4219508
    Abstract: This invention relates to an improved process for the preparation of a mixture of various low molecular weight hydroxyaldehydes, hydroxyketones and polyhydric alcohols by the condensation of formaldehyde with itself. The essential feature of the improvement is that unpurified synthesis gases of the kind obtained from the large scale industrial production of formaldehyde can be used directly as the source of formaldehyde.
    Type: Grant
    Filed: August 30, 1977
    Date of Patent: August 26, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kuno Wagner
  • Patent number: 4217290
    Abstract: This invention consists of a process for preparing bifunctional aliphatic organic compounds of at least 6 carbon atoms, wherein a cycloaliphatic oxyhydroperoxide is reacted with an alpha-olefine having its double bond activated by a conjugate electron-attracting group, in the presence of a bivalent Cr salt, a bivalent V salt or a trivalent Ti salt.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: August 12, 1980
    Assignee: Brichima S.p.A.
    Inventors: Paolo Maggioni, Francesco Mauri, Attilio Citterio
  • Patent number: 4216144
    Abstract: Iron proteinates or chelates of iron with hydrolyzed protein which are usually insoluble are rendered soluble without destroying the chelate and are more readily assimilable by plant and animals.
    Type: Grant
    Filed: October 20, 1977
    Date of Patent: August 5, 1980
    Inventor: Harvey H. Ashmead
  • Patent number: 4216143
    Abstract: Non-ferrous metal proteinates or chelates of essential bivalent metals with hydrolyzed protein are rendered soluble without destroying the chelate and are more readily assimilated by plants and animals.
    Type: Grant
    Filed: October 20, 1977
    Date of Patent: August 5, 1980
    Inventor: Harvey H. Ashmead
  • Patent number: 4206231
    Abstract: A 2-hydrazonopropionic acid derivative of the formula ##STR1## wherein R is an aliphatic hydrocarbon radical, andX is a valency bond or a divalent aliphatic hydrocarbon radical containing up to 4 carbon atoms, with the proviso that when X is a valency bond, R cannot be saturated cycloalkyl, ora physiologically compatible salt, lower alkyl ester or amide thereof, which exhibit hypoglycaemic activity.
    Type: Grant
    Filed: August 17, 1978
    Date of Patent: June 3, 1980
    Assignee: Boehringer Mannheim GmbH
    Inventors: Rainer Haeckel, Michael Oellerich, Ruth Heerdt, Manfred Hubner, Felix H. Schmidt
  • Patent number: 4194050
    Abstract: Enamides are prepared by hydrogenating oximes having at least one hydrogen atom at the .alpha.-position in the presence of a carboxylic anhydride using a ruthenium catalyst. These enamides are important to obtain amino group-containing compounds by reduction or polymerization.
    Type: Grant
    Filed: July 13, 1978
    Date of Patent: March 18, 1980
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Motoo Hazama
  • Patent number: 4172072
    Abstract: Protein sources are subjected to hydrolysis by the action of specific proteases under neutral conditions and are then reacted with water soluble bivalent metal salts in an aqueous alkaline media to form metal proteinates which are then buffered thereby forming biologically acceptable metal proteinates which are protected from adverse acid or alkaline destruction.
    Type: Grant
    Filed: October 20, 1977
    Date of Patent: October 23, 1979
    Inventor: Harvey H. Ashmead