Patents Assigned to Duphar International Research B.V.
  • Patent number: 5348949
    Abstract: The invention relates to a method of preparing N-oxo-tetrahydro-.beta.-carbolines having formula 1. ##STR1## by an intramolecular ringclosure reaction of compounds of formula 2. ##STR2## wherein Z is an aldehyde function or acetal function, or is a functional group which can be converted into such a function during the ringclosure reaction.The eudistomin derivatives within the group of compounds having formula 1 have strong antiviral and antitumour activity.
    Type: Grant
    Filed: February 12, 1993
    Date of Patent: September 20, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Peter H. H. Hermkens, Jan H. Van Maarseveen, Johan W. Scheeren, Cornelis G. Kruse
  • Patent number: 5342958
    Abstract: Compounds of the formula ##STR1## wherein A is a hydrogen atoms, a halogen atom, a methyl group, or a methoxy group;B is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, with the proviso that A and B ar not both a hydrogen atom;X and Y each are an oxygen atom or a sulfur atom;R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonyl group;R.sub.1 is a hydrogen atom, an alkyl group, a halogen substituted alkyl group, an alkoxy substituted alkyl group, an alkylthio substituted alkyl group, a cyano substituted alkyl group, a 1-cycloalkenyl group, a benzyl group, a halogen substituted benzyl group, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsulfonyl group, while furthermore R and R.sub.1 together with the group ##STR2## indicated in the above formula may form a ring system; and R.sub.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: August 30, 1994
    Assignee: Solvay Duphar International Research B.V.
    Inventors: Kobus Wellinga, Rudolf Mulder
  • Patent number: 5332746
    Abstract: The invention relates to a group of new 8,9-annelated-.beta.-carbolines and 8,9-annelated-3,4-dihydro-.beta.-carbolines having interesting fibrinolytic properties. In particular the compounds can be used as orally active fibrinolytics.The compounds have the general formulae 1 and 2 ##STR1## wherein R.sub.2 +R.sub.3 together with the carbon atom and the nitrogen atom to which they are bound and the intermediate carbon atom constitute a heterocyclic group consisting of 5-10 ring atoms.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: July 26, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Derk Hamminga, Hans H. Haeck, Ineke van Wijngaarden, Johannes W. C. M. Jansen
  • Patent number: 5329023
    Abstract: The invention relates to a method of preparing optically active alcohols which consist substantially (at least 75% e.e.) or entirely of one enantiomer of formula 4 ##STR1## wherein R and A are as defined therein. The method comprises, which maintaining enantiomeric excess, converting an optically active cyanohydrin of formula 1 ##STR2## into optically active protected cyanohydrin of formula 2 ##STR3## converting the protected cyanohydrin of formula 2 into an optically active compound of formula 3 ##STR4## removing the protecting group B.
    Type: Grant
    Filed: June 15, 1992
    Date of Patent: July 12, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Johannes Brussee, Arne Van Der Gen
  • Patent number: 5328905
    Abstract: New 8,9-annelated-1,2,3,4-tetrahydro-.beta.-carboline derivatives of the formula ##STR1## wherein R.sub.1 -R.sub.7 are as defined herein; and pharmaceutically acceptable salts and prodrugs thereof. A method of dissolving blood clots using this compound and a pharmaceutical composition having fibrinolytic activity comprising this compound are also part of the present invention.
    Type: Grant
    Filed: December 23, 1991
    Date of Patent: July 12, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Derk Hamminga, Ineke van Wijngaarden, Johannes W. C. M. Jansen
  • Patent number: 5326405
    Abstract: The present invention is concerned with a method for the preparation of crystal-water-free crystalline lactulose by subjecting an aqeous solution or suspension of lactulose to simultaneous reduction of the water content by evaporation and continuous stirring, optionally in the presence of seed crystals, until a free-flowing solid powder is obtained.
    Type: Grant
    Filed: October 9, 1991
    Date of Patent: July 5, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Henk Pluim, Jan G. Kraaijenbrink
  • Patent number: 5326768
    Abstract: The present invention concerns 3,4-annelated benzimidazol-2(1H)-one 1-carboxylic acid derivatives of the formula ##STR1## wherein R.sub.0, Z, A, B and C are as defined herein. Such derivatives are useful in the treatment of symptoms which are caused by over-excitation of 5-hydroxytryptamine receptors.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: July 5, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Ineke Van Wijngaarden, Derk Hamminga, Wouter Wouters
  • Patent number: 5304291
    Abstract: The invention relates to a method of preparing a 9beta,10alpha-5,7-diene steroid by irradiating the corresponding 9alpha,10beta-5,7-diene steroid with filtered ultraviolet light from an indium lamp.
    Type: Grant
    Filed: February 24, 1993
    Date of Patent: April 19, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Berthus Bout, Ronald Voorhaar
  • Patent number: 5296497
    Abstract: The invention relates to 3,4-dehydropiperidine derivatives having psychotropic activity, which compounds are represented by the general formula 1 ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.3 alkyl;R.sub.2 is hydrogen, an unsubstituted or substituted C.sub.1 -C.sub.10 hydrocarbon group, or a group of the general formula ##STR2## wherein A is C.sub.2 -C.sub.10 alkylene,R.sub.5 is hydrogen or C.sub.1 -C.sub.3 alkyl, andR.sub.6 is unsubstituted or substituted aryl or heteroaryl, hydrocarbon, substituted or unsubstituted (hetero)aralkyl, or substituted or unsubstituted heterocyclic; or wherein R.sub.5 and R.sub.6 together with the carbamoyl group to which they are bound constitute a heterocyclic ring system;n has the value 1 or 2; andZ is a heterocyclic group.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: March 22, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Jan Hartog, Roelof Van Hes, Berend Olivier, Ineke Van Wijngaarden
  • Patent number: 5281595
    Abstract: The invention relates to compounds having anti-ischaemic activity, memory enhancing activity and anti-convulsive activity of the formulae 1A and 1B ##STR1## wherein R.sub.1 +R.sub.2 together form an alkylene group having 1-3 C-atoms which may be substituted with one or more alkyl group(s) having 1-3 C-atoms and the remaining R and Z variables are defined as disclosed herein, or a pharmacologically acceptable salt thereof.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: January 25, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Josephus H. M. Lange, Gerrit P. Toorop, Ineke v. Wijngaarden, Jacobus A. J. den Hartog
  • Patent number: 5273544
    Abstract: The present invention relates to an injection device for the automatic injection of at least one injection liquid, comprising an assembly of a discharge mechanism, a cartridge holder and a cartridge slidably accommodated in the cartridge holder, the discharge mechanism comprising an outer sleeve wherein the cartridge holder is slidably adapted. A protective cover is provided on the front of the device, covering the front portions of the cartridge holder and the outer sleeve in such a manner, that unintentional backward movement of the cartridge holder in the outer sleeve, resulting in activation of the device, is prevented.
    Type: Grant
    Filed: June 10, 1992
    Date of Patent: December 28, 1993
    Assignee: Duphar International Research B.V.
    Inventor: Gillis P. van der Wal
  • Patent number: 5266589
    Abstract: The invention relates to a method of improving the growth and the feed efficiency and of increasing the muscle/fat ratio of agricultural domestic animals, in particular bovine animals and sheep, by administering to the animals a composition which comprises as an active substance a compound of the general formula ##STR1## wherein: R.sub.1 is a phenylalkyl group the alkyl group of which comprises 1-3 carbon atoms and the phenyl group of which may be substituted with one or more substituents selected from the group consisting of hydroxy, methoxy, fluoro and methylsulphonylamino, or whereinR.sub.1 is a thienyl alkyl group or a tetrahydrofurylalkyl group the alkyl group of which comprises 1-3 carbon atoms; or whereinR.sub.1 is an optionally branched alkyl group having 1-8 carbon atoms which optionally is substituted with a C.sub.1 -C.sub.4 alkoxy group, a hydroxy group, a C.sub.1 -C.sub.4 alkoxycarbonyl group or a carboxy group; and whereinR.sub.2 and R.sub.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: November 30, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Johan K. Van Dasler, Jan Van Dijk
  • Patent number: 5252191
    Abstract: The invention relates to a method for the photochemical isomerization of organic compounds, in particular for the photochemical conversion of tachysterol compounds into previtamin D compounds and of trans-vitamin D compounds into cis-vitamin D compounds, under the influence of radiation, by exposing a solution of the organic compound to be converted in the presence of a non-polymeric photosensitizer to light with approx. 300-1,000 nm wavelength, and by then isolating the resulting product, wherein a substituted thiophene derivative having a substantial absorption in said wavelength region is used as the photosensitizer. The invention also relates to a new photosensitizer to be used for said isomerization reaction.
    Type: Grant
    Filed: April 24, 1991
    Date of Patent: October 12, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Louis F. Pauli, Alphons Dufourny, Robert B. Koolstra, Hans Wynberg, Wolter Ten Hoeve
  • Patent number: 5245071
    Abstract: Compounds of the formula ##STR1## wherein A is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group;B is a hydrogen atom, a halogen atom, a methyl group, or a methoxy group, with the proviso that A and B ar not both a hydrogen atom;X and Y each are an oxygen atom or a sulfur atom;R is a hydrogen atom, an alkyl group, a hydroxy group, an alkoxy group, an alkoxymethyl group, an acyl group, or an alkoxycarbonyl group;R.sub.1 is a hydrogen atom, an alkyl group, a halogen substituted alkyl group, an alkoxy substituted alkyl group, an alkylthio substituted alkyl group, a cyano substituted alkyl group, a 1-cycloalkenyl group, a benzyl group, a halogen substituted benzyl group, a hydroxy group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an alkoxythiocarbonyl group, an alkylsulfonyl group, or a phenylsulfonyl group, while furthermore R and R.sub.1 together with the group ##STR2## indicated in the above formula may form a ring system; and R.sub.
    Type: Grant
    Filed: June 3, 1992
    Date of Patent: September 14, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Kobus Wellinga, Rudolf Mulder
  • Patent number: 5223625
    Abstract: The invention relates to a group of new annelated indolo [3,2-c] lactam derivatives of the formula ##STR1## having an antagonistic activity on 5-HT receptors. The compounds can be used for the treatment of symptoms which are caused by excessive stimulation of said receptors in the gastrointestinal system, the central nervous system, the cardiovascular system, the respiratory system, and for alleviating or preventing withdrawal symptoms which are induced by abuse of drugs.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: June 29, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Ineke Van Wijngaarden, Hans H. Haeck, Derk Hamminga, Wouter Wouters
  • Patent number: 5219325
    Abstract: The invention relates to a wound dresssing comprising (1) a lower layer of a hydrogel of a polymer cross-linked under the influence of electron beam (E.B.) radiation, to which optionally one or more medicinal and/or antibacterial agents and/or one or more auxiliary substances have been added, and (2) a polymeric top layer, in which the top layer consists at least substantially of an elastomer selected from the group consisting of a silicone rubber, a polyetherpolyurethane copolymer, a polyester-polyurethane copolymer, a polyether-polyester copolymer and an optionally modified block copolymer based on suitable vinyl monomers, and that a fibrous layer is provided between the lower layer and the top layer for bonding the two layers together.The invention further relates to a method of preparing said wound dressing.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: June 15, 1993
    Assignee: Duphar International, Research B.V.
    Inventors: Wilhelmus E. Hennink, Jacobus J. Zandman, Maria E. van der Heijden-van Beek, Hendrik Teunissen
  • Patent number: 5219575
    Abstract: The present invention relates to compositions having a controlled zero-order delivery rate of the active component. The composition comprises a core or a protective layer coated with a continuous matrix of constant composition containing such a mixture of active substance(s) and excipient(s) that the concentration of the active substance(s) decreases from the core or the protective layer towards the outside, and the concentration of the excipient(s) increases in the same direction, whereas the sum of two substantially remains constant over the whole distance.
    Type: Grant
    Filed: August 20, 1990
    Date of Patent: June 15, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Elvira M. G. Van Bommel, Jasper G. Fokkens
  • Patent number: 5217129
    Abstract: The invention relates to a vial for storing a substance in a condition in which it is excludeded from the ambient air, comprising a reservoir having a closed end and an open end, the open end communicating with a closable tubular member via a neck portion. The vial comprises a cap having a central aperture which is sealingly but detachably connected to the neck portion of the reservoir, while the tubular member constitutes a separate component of the vial and is proportioned so that it can be connected in the aperture of the cap in a circumferentially sealing manner, a rear end portion of the tubular member extending within the neck portion of the reservoir and a front portion which comprises a sealing means extending beyond the reservoir.
    Type: Grant
    Filed: November 6, 1991
    Date of Patent: June 8, 1993
    Assignee: Duphar International Research B.V.
    Inventor: Arnoldus Portengen
  • Patent number: 5212197
    Abstract: The invention relates to new, fungicidally active pyrazole compounds of the general formula ##STR1## wherein Ar is an unsubstituted phenyl group or a phenyl group, substituted with 1 or 2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen, nitro, cyano and C.sub.1 -C.sub.4 alkoxy, or with 3 halogen atoms,R is a C.sub.1 -C.sub.12 alkyl group,R.sub.1 is a C.sub.1 -C.sub.4 alkyl group, andY is CH or N.The invention also relates to new imidazolylvinyldithioacetals, suitable as starting materials for preparing said new pyrazole compounds and also having fungicidal activity.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: May 18, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Hendrik Dolman, Johannes Kuipers, Leonarda C. Niemann, Bart Heijne
  • Patent number: 5198437
    Abstract: 1,7-Annelated esters and amides of indolecarboxylic acids having formula 2, ##STR1## wherein R.sub.1 is halogen;n has a value of 0-2;Z together with the carbon atom, the nitrogen atom and the intermediate carbon atom, forms a heterocyclic group consisting of 6 ring atoms in which, besides the nitrogen atom already present, a second hetero atom of S is present, which ring may be annelated with a benzene ring;R.sub.3 is hydrogen, halogen, alkyl, alkoxy or alkylthio having 1-4 carbon atoms; andR.sub.2 is a group --CO--Y--R.sub.7 wherein Y is an oxygen atom, or a group --NR.sub.6, wherein R.sub.6 is hydrogen or alkyl having 1-3 C-atoms, and R.sub.7 represents a group of the formula ##STR2## wherein p has the value 1 or 2, q has the value 2 or 3, R.sub.8 is hydrogen or alkyl or hydroxyalkyl having 1 or 2 C-atoms, r is 0 or 1, and R.sub.10 is absent.
    Type: Grant
    Filed: December 17, 1990
    Date of Patent: March 30, 1993
    Assignee: Duphar International Research B.V.
    Inventors: Derk Hamminga, Hans H. Haeck, Ineke Van Wijngaarden, Wouter Wouters