Patents Assigned to U.C.B. Societe Anonyme
  • Patent number: 4943639
    Abstract: (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide, its preparation and pharmaceutical compositions containing the same. It can be prepared either by reacting (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid successively with an alkyl haloformate and with ammonia, or, by cyclizing an (S)-2-amino-butanamide of the formula X--CH.sub.2 CH.sub.2 --Y--NHCH(C.sub.2 H.sub.5)CONH.sub.2 wherein Y is a --CH.sub.2 -- radical when X represents a ZOOC-- radical and Y is a --CO-- radical when X represents a HalCH.sub.2 -- radical, Z being a C.sub.1 -C.sub.4 alkyl radical and Hal a halogen atom.This laevorotatory enantiomer has been found to have significantly higher protective activity against hypoxia and ischemia than the corresponding racemate.
    Type: Grant
    Filed: February 16, 1989
    Date of Patent: July 24, 1990
    Assignee: U C B Societe Anonyme
    Inventors: Jean Gobert, Jean-Pierre Geerts, Guy Bodson
  • Patent number: 4923865
    Abstract: New substituted 1-(1H-imidazol-4-yl)alkyl-benzamides and their salts, processes for the preparation thereof and pharmaceutical compositions.These compounds have the formula ##STR1## wherein R.sub.1, R.sub.2 =hydrogen or C.sub.1 -C.sub.4 -alkyl,R.sub.3 =hydrogen, amino, hydroxyl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl,R.sub.4 =hydrogen or C.sub.1 -C.sub.4 -alkyl, orR.sub.3 R.sub.4 N=pyrrolidino, piperidino or morpholino,R.sub.5 and R.sub.6 =hydrogen, hydroxyl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, at least one ofR.sub.5 and R.sub.6 being other than hydrogen.These compounds are prepared either by reacting a nitrogen compound with an alkyl 1-(1H-imidazol-4-yl)alkyl-benzoate or with a 1-(1H-imidazol-4-yl)alkyl-benzoic acid, or by hydrolyzing in an acid medium a 2-hydroxy-3-[1-(1H-imidazol-4-yl)alkyl]-benzonitrile.The compounds have anti-ischemic and .alpha..sub.2 -adrenoceptor agonist activities.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: May 8, 1990
    Assignee: U C B Societe Anonyme
    Inventors: Eric Cossement, Jean-Pierre Geerts, Jean Gobert, Philippe Michel, Ernst Wulfert
  • Patent number: 4696943
    Abstract: (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide, its preparation and pharmaceutical compositions containing the same. It can be prepared either by reacting (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid successively with an alkyl haloformate and with ammonia, or, by cyclizing an (S)-2-aminobutanamide of the formula X--CH.sub.2 CH.sub.2 --Y--NHCH(C.sub.2 H.sub.5)CONH.sub.2 wherein Y is a --CH.sub.2 -- radical when X represents a ZOOC-- radical and Y is a --CO-- radical when X represents a HalCH.sub.2 -- radical, Z being a C.sub.1 -C.sub.4 alkyl radical and Hal a halogen atom.This laevorotatory enantiomer has been found to have significantly higher protective activity against hypoxia and ischemia than the corresponding racemate.
    Type: Grant
    Filed: May 14, 1985
    Date of Patent: September 29, 1987
    Assignee: U C B Societe Anonyme
    Inventors: Jean Gobert, Jean-Pierre Geerts, Guy Bodson
  • Patent number: 4546076
    Abstract: An enzymatic process for the determination of beta-lactam antibiotics in a biological liquid, comprising the steps of: (1) incubating the liquid with soluble D-alanyl-D-alanine-carboxypeptidase produced by Actinomadura R 39, said enzyme being immobilized on a water-insoluble support, the beta-lactam antibiotic reacting with the immobilized enzyme to form an inactive and equimolecular enzyme-antibiotic complex; (2) separating the immobilized enzyme from the liquid and washing it; (3) incubating the immobilized enzyme with a substrate solution to hydrolyze it and form an amount of D-alanine corresponding to the residual enzymatic activity; (4) determining the amount of D-alanine formed; and (5) comparing the determination of step (4) with a standard to obtain the concentration of the antibiotic in the biological liquid; as well as a test set for carrying out this process and comprising the necessary reagents.
    Type: Grant
    Filed: January 31, 1983
    Date of Patent: October 8, 1985
    Assignee: U C B Societe Anonyme
    Inventors: Jacques Degelaen, Albert Loffet, Jean-Pierre Durieux
  • Patent number: 4271172
    Abstract: 6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, salts and esters thereof of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl or an alkali metal or ammonium ion and R.sub.2 is methyl, phenyl or benzyl and process for preparing the same.These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to penicillins, besides own antibiotic activity with a broad antibacterial spectrum. Therefore, they are useful as antibacterials agents and as therapeutic agents for humans and for animals in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.
    Type: Grant
    Filed: June 24, 1980
    Date of Patent: June 2, 1981
    Assignee: U C B Societe Anonyme
    Inventors: Ludovic Rodriguez, Jacques Leclercq, Pierre Ykman, Eric Cossement
  • Patent number: 4271173
    Abstract: 6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acid derivatives having the formula ##STR1## wherein R is a methyl, phenyl or benzyl radical, Z.sub.1 is a hydrogen atom and Z.sub.2 is a radical selected from those known from penicillin chemistry and is preferably a 2-phenylacetyl, 2-amino-2-phenylacetyl, 5-methyl-3-phenyl-4-isoxazolecarbonyl or 2,6-dimethoxybenzoyl radical, or Z.sub.1 and Z.sub.2 together represent a bivalent radical Z.sub.3 and preferably a (hexahydro-1H-azepin-1-yl)methylene radical, as well as the pharmaceutically acceptable non-toxic salts thereof and process for preparing the same.These compounds have valuable antibacterial properties and are useful as therapeutic agents in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.
    Type: Grant
    Filed: June 24, 1980
    Date of Patent: June 2, 1981
    Assignee: U C B, Societe Anonyme
    Inventors: Ludovic Rodriguez, Jacques Leclercq, Pierre Ykman, Eric Cossement
  • Patent number: 4216339
    Abstract: The invention relates to an improved process for the production of methyl formate, wherein a current of a gas containing carbon monoxide is reacted at elevated temperature (70.degree.-110.degree. C.) and pressure (20-110 bars) in a reaction zone with a recycled current of liquid reaction mixture containing(a) methanol(b) an alkali metal or alkaline earth metal methoxide as catalyst, and(c) methyl formate produced as reaction product,part of the current of liquid reaction mixture being withdrawn in order to recover methyl formate therefrom.The characteristic feature of the invention consists in that the recycled liquid reaction mixture is used for sucking and dispersing the current of gas in the reaction mixture. Advantages of the process are: excellent heat exchange, high productivity, absence of solid deposits on the internal surfaces of the apparatus, lower operating pressures and temperatures, use of apparatus of smaller dimensions, suppression of recycling of carbon monoxide, etc.
    Type: Grant
    Filed: March 10, 1977
    Date of Patent: August 5, 1980
    Assignee: U C B, Societe Anonyme
    Inventors: Willy Couteau, Jean Ramioulle
  • Patent number: 4216221
    Abstract: A 1,3-disubstituted urea or 2-thiourea having the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.6, R.sub.7 and R.sub.8 represent independently a hydrogen atom, an alkyl radical containing 1 to 4 carbon atoms, an alkenyl radical containing 2 to 4 carbon atoms, an alkylene radical forming together with the carbon atom to which it is attached a cycloalkane ring having 5 or 6 carbon atoms, an aryl radical or a substituted aryl radical, R.sub.4 and R.sub.5 represent independently a hydrogen atom, an alkyl radical containing 1 or 2 carbon atoms or a phenyl radical, n and q are independently a whole number of from 3 to 7, m and p are independently 0, 1 or 2 and X is an oxygen or a sulfur atom, processes for the preparation thereof and pharmaceutical compositions containing the same.
    Type: Grant
    Filed: February 9, 1978
    Date of Patent: August 5, 1980
    Assignee: U C B, Societe Anonyme
    Inventor: Jean de Lannoy
  • Patent number: 4206025
    Abstract: Radio-hardenable acrylic polyesters of the general formula:[A][B--C--D.sub.m ].sub.2 (I)wherein A is the radical of a linear polyester of the general formula:--O--[R.sub.1 --R.sub.2 ].sub.x R.sub.1 --O-- (II)wherein R.sub.1 is a radical derived from at least one dihydroxylated compound, R.sub.2 a radical derived from at least one dicarboxylic acid and x an integer from 1 to 20; wherein B has the same meaning as R.sub.2, C is a radical derived from at least one aliphatic polyhydroxylated compound, D a radical derived from acrylic acid and m is an integer from 2 to 7.Manufacture of said polyesters and use as binders in radio-hardenable compositions.
    Type: Grant
    Filed: September 5, 1978
    Date of Patent: June 3, 1980
    Assignee: U C B, Societe Anonyme
    Inventors: August Vrancken, Paul Dufour
  • Patent number: 4181239
    Abstract: A cylindrical container body for packaging pressurized carbonated beverages, comprising (a) at least one film of a synthetic or semi-synthetic organic polymer having a permeability to oxygen lower than 6.times.10.sup.-13 ml.cm/cm.sup.2.sec.cm of mercury at 25.degree. C. and 0% relative air humidity; (b) at least two films of a polyester; and (c) at least two layers of an organic thermoplastic binder having a permeability to water vapor lower than 1.times.10.sup.-14 g.cm/cm.sup.2.sec.cm of mercury at 38.degree. C.
    Type: Grant
    Filed: March 8, 1978
    Date of Patent: January 1, 1980
    Assignee: U C B, Societe Anonyme
    Inventors: Robert Heiremans, Andre Depuydt
  • Patent number: 4155919
    Abstract: Process for the catalytic hydrogenolysis of maleic anhydride to give 1,4-butanediol and tetrahydrofuran in a single-stage operation by means of hydrogen under heat and pressure, in the presence of a suspension of a reduced solid catalyst, which contains as catalytically active elements Ni in association with Mo and/or W and optionally with Zr and/or Nb, having the following essential characteristics: (I) double oxidizing treatment of the solid catalyst in two stages before its reduction, and (II) conducting the hydrogenolysis of maleic anhydride at a temperature of from 170.degree. to 215.degree. C. under a hydrogen pressure below about 200 bars, in a reaction medium which contains gamma-butyrolactone, for a time such that the amount of gamma-butyrolactone in the final reaction medium is substantially equal to that present in the initial reaction medium.
    Type: Grant
    Filed: November 21, 1977
    Date of Patent: May 22, 1979
    Assignee: U C B Societe Anonyme
    Inventors: Jean Ramioulle, Willy Couteau
  • Patent number: 4139628
    Abstract: Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic acid derivatives having the formula ##STR1## WHEREIN X is a sulfur or oxygen atom or the sulfinyl group, n is 1 or 2, m is 1 or 2, R.sub.1 is hydrogen, R.sub.2 is one of the radicals known in the chemistry of the penicillins, preferably 2-phenylacetyl, 2-amino-2-phenylacetyl, 5-methyl-3-phenyl-4-isoxazolecarbonyl or 2,6-dimethoxybenzoyl, or R.sub.1 and R.sub.2 together represent a bivalent radical R.sub.3, preferably (hexahydro-1H-azepin-1-yl)methylene and their therapeutically acceptable non-toxic salts and process for preparing the same.These compounds have valuable antibacterial properties and are useful as therapeutic agents in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: February 13, 1979
    Assignee: U C B, Societe Anonyme
    Inventors: Ludovic Rodriguez, Jacques Leclercq, Pierre Ykman, Eric Cossement
  • Patent number: 4137236
    Abstract: Amino-spiro[oxa(or thia)cycloalkane-penam]-carboxylic acid, a salt or an ester thereof, of the formula ##STR1## wherein Z is a hydrogen or an alkali metal atom, or a group protecting the carboxylic function, X is a sulfur or oxygen atom, n is 1 or 2, m is 1 or 2, and process of preparing the same.These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to penicillins, besides own antibiotic activity with a broad antibacterial spectrum.
    Type: Grant
    Filed: January 16, 1978
    Date of Patent: January 30, 1979
    Assignee: U C B, Societe Anonyme
    Inventors: Ludovic Rodriguez, Jacques Leclerca, Pierre Ykman, Eric Cossement
  • Patent number: 4115579
    Abstract: A process of inhibiting blood platelet aggregation, without undesirable side effects on the mechanism of coagulation, wherein an effective amount of 2-oxo-1-pyrrolidineacetamide, 2-(2-oxo-pyrrolidino)-propionamide or 2-(2-oxo-pyrrolidino)-butyramide is administered to a man requiring such inhibition. Useful in the prophylactic treatment of vascular diseases, in surgical operations and the like, to inhibit the tendency of blood platelets to aggregate.
    Type: Grant
    Filed: October 19, 1977
    Date of Patent: September 19, 1978
    Assignee: U C B, Societe Anonyme
    Inventor: Joseph Strubbe
  • Patent number: 4091027
    Abstract: 6'-Amino-spiro[cycloalkane-1,2'-penam]-3'-carboxylic acids of the formula ##STR1## WHEREIN Z is a hydrogen or an alkali metal atom, or a protective group, and n a whole number of from 3 to 6, and process of preparing the same.These compounds are useful as intermediates in the synthesis of a new group of antibiotics having properties similar to the penicillins.
    Type: Grant
    Filed: May 24, 1977
    Date of Patent: May 23, 1978
    Assignee: U C B Societe Anonyme
    Inventors: Ludovic Rodriguez, Jacques Leclercq
  • Patent number: 4085159
    Abstract: Process for the preparation of powdered thermosetting coating composition suitable for application as paint or varnish on electricity-conducting articles by powder spray methods and fluidized bed coating processes, which comprises: in a first stage, preparing a branched-chain hydroxyl group-containing polyester from at least one dicarboxylic organic acid, at least one polycarboxylic aromatic acid and at least one dihydric organic compound; in a second stage, esterifying the hydroxyl group-containing polyester thus obtained with an aromatic or hydroaromatic dicarboxylic acid to give a carboxyl group-containing polyester having an acid number which is substantially equal to the hydroxyl number of the hydroxyl group-containing polyester obtained in the first stage; and in a third stage, homogenously mixing the carboxyl group-containing polyester obtained in the second stage with an epoxy compound containing at least two epoxy groups, and optionally adding auxiliary substances conventionally used in the manufactu
    Type: Grant
    Filed: April 28, 1976
    Date of Patent: April 18, 1978
    Assignee: U C B, Societe Anonyme
    Inventor: Arthur Marsiat
  • Patent number: 4082710
    Abstract: Isocyanate-modified compounds consisting of the reaction products of an organic isocyanate with compounds with multiple acrylic radicals, the average composition of which has the general formula:X--Y--(Z).sub.m-p-1 ].sub.nwhereinX is the radical derived by removing the OH groups from the carboxyl groups of an organic carboxylic acid containing n COOH groups and the number of carbon atoms of which is between 14 and 90,Y is the radical derived by removing m-p hydrogen atoms from the hydroxyl groups of an organic compound containing m OH groups,Z is the monovalent radical derived by removing the OH group from the carboxyl group of a monocarboxylic acid having at least one terminal CH.sub.2 .dbd.CH--COO-- radical,n is a whole number from 1 to 6,m is a whole number from 2 to 8, andp is a number of from 0 to 2.
    Type: Grant
    Filed: December 3, 1975
    Date of Patent: April 4, 1978
    Assignee: U C B, Societe Anonyme
    Inventors: August Vrancken, Paul Dufour, Jacques Noat, Jean Holderic
  • Patent number: 4080449
    Abstract: New physiologically active 1,2,4,5-tetrahydro-3H-2-benzazepin-3-ones having the general formula ##STR1## wherein R.sub.1 is hydrogen or phenyl, R.sub.2 is hydrogen, alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.1 -C.sub.4 -acyl, hydroxyalkyl, alkoxyalkyl, mono- or dialkylaminoalkyl, cyanoalkyl, alkoxyacetyl, carbamoylalkyl, acetamido-C.sub.2 -C.sub.5 -alkyl, alkoxycarbonylalkyl or (tetrahydro-2H-pyran-2-yloxy)alkyl, the alkyl and the alkoxy radicals having 1 to 5 carbon atoms, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl, R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkoxy and R.sub.8 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl, at least one of the symbols R.sub.1 to R.sub.8 being other hydrogen, processes for the preparation thereof and pharmaceutical compositions containing the same. In particular, the compounds of this invention are useful in the treatment of memory disorders.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: March 21, 1978
    Assignee: U C B, Societe Anonyme
    Inventors: Paul Croisier, Ludovic Rodriquez
  • Patent number: 4080450
    Abstract: New physiologically active 2-carbamoyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-ones having the general formula ##STR1## wherein R.sub.1 is hydrogen or phenyl, R.sub.2 is morpholino or amino mono- or di-substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl or phenyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.5 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.7 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkoxy, R.sub.8 is hydrogen, halogen or C.sub.1 -C.sub.4 -alkyl, processes for the preparation thereof and pharmaceutical compositions containing the same. In particular, the compounds of this invention are useful in the treatment of memory disorders.
    Type: Grant
    Filed: July 27, 1977
    Date of Patent: March 21, 1978
    Assignee: U C B, Societe Anonyme
    Inventors: Paul Croisier, Ludovic Rodriguez
  • Patent number: 4077951
    Abstract: L-pyroglutamyl-L-prolinamide is useful for correcting metabolic or endocrinal disorders connected with senescence. It can be prepared by reacting L-pyroglutamic acid with L-prolinamide.
    Type: Grant
    Filed: July 7, 1976
    Date of Patent: March 7, 1978
    Assignee: U C B Societe Anonyme
    Inventor: Albert Loffet