Nitrogen Double Bonded Directly At 2-position Of The Diazole Ring, Or Tautomeric Equivalent Patents (Class 514/388)
  • Patent number: 5763469
    Abstract: The present invention relates to substituted cyclic ureas and analogs thereof of formula (I): ##STR1## wherein, T is selected from: --N(R.sup.22)C(.dbd.Z)N(R.sup.23)--; --N(R.sup.22)C(.dbd.Z)C(.dbd.Z)N(R.sup.23)--; --N(R.sup.22)S(.dbd.Z')N(R.sup.23)--; --N(R.sup.22)S(.dbd.Z').sub.2 N(R.sup.23)--; or --N(R.sup.22)P(.dbd.O)(R.sup.24a)N(R.sup.23)--;Z is O, S, NR.sup.24 ; and,Z' is O or NR.sup.24 ;or pharmaceutically acceptable salt forms or prodrugs thereof, which are useful as retroviral protease inhibitors, and to pharmaceutical compositions comprising such compounds and methods of using the same for treating viral infection.
    Type: Grant
    Filed: August 21, 1996
    Date of Patent: June 9, 1998
    Assignee: The DuPont Merck Pharmaceutical Company
    Inventor: George Vincent Delucca
  • Patent number: 5744494
    Abstract: The anthelmintic efficacy in animals and humans of a benzimidazole such as fenbendazole, albendazole, oxfendazole or trichlabendazole is potentiated by use with piperonyl butoxide or other methylenedioxyphenyl synergist.
    Type: Grant
    Filed: July 25, 1995
    Date of Patent: April 28, 1998
    Assignee: British Technology Group Limited
    Inventors: Quintin Archibald McKellar, Hafid Abdelaali Benchaoui
  • Patent number: 5741804
    Abstract: This invention relates to compounds of the formula: ##STR1## which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, and a method for inhibiting platelet aggregation.
    Type: Grant
    Filed: May 30, 1995
    Date of Patent: April 21, 1998
    Assignee: SmithKline Beecham Corporation
    Inventors: Richard McCulloch Keenan, William Henry Miller
  • Patent number: 5693661
    Abstract: Certain vinyl acetylene benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 2, 1997
    Assignee: Eli Lilly and Company
    Inventors: Shawn C. Miller, Frantz Victor, Wayne A. Spitzer, Thomas R. Sattelberg, Sr., Mark J. Tebbe
  • Patent number: 5670485
    Abstract: The present invention is directed to anticoccidial methods, animal feed premixes, and animal feeds, employing a specified o-phenylenediamine or benzimidazole. The present invention is also directed to anticoccidial methods, animal feed premixes, and animal feeds employing two active agents. In such combined therapy, a first substance is a polyether antibiotic, and the second substance is a designated, benzimidazoline.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: September 23, 1997
    Assignee: Eli Lilly and Company
    Inventor: George O. P. O'Doherty
  • Patent number: 5569671
    Abstract: Novel compounds of formula I ##STR1## wherein R.sup.1 is independently hydrogen, hydroxy, alkyl with 1 to 6 carbon atoms, acyloxy groups with 1 to 6 carbon atoms, alkyloxy with 1 to 6 carbon atoms or from 1 to 5 sugar moieties; and R.sup.2 is independently hydrogen, or alkyl with 1 to 6 carbon atoms.The compounds are producible by aerobic cultivation on suitable nutrient media under suitable conditions of a strain of the fungus Ascochyta sp., subsequent recovery of the active component from the fermentation medium, and optionally modifying the active compound to obtain a compound of the desired formula I.Disclosed is also microorganisms capable of producing said compounds, compositions containing said compounds, and the use of such compositions for controlling fungi in valuable crops, animals, including birds and mammals, and in the preservation of wood, paints and edible products.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: October 29, 1996
    Assignee: Novo Nordisk A/S
    Inventors: Ruby I. Nielsen, Frank W. Rasmussen
  • Patent number: 5552422
    Abstract: The invention encompasses the novel compound of Formula I as well as a method of treating cyclooxygenase-2 mediated diseases comprising administration to a patient in need of such treatment of a non-toxic therapeutically effective amount of a compound of Formula I. ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: January 11, 1995
    Date of Patent: September 3, 1996
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Jacques Y. Gauthier, Cheuk K. Lau, Yves LeBlanc, Chun-Sing Li, Patrick Roy, Michel Therien, Zhaoyin Wang
  • Patent number: 5545653
    Abstract: The present application provides a series of benzimidazole compounds which inhibit the growth of picornaviruses, such as rhinoviruses, enteroviruses, cardioviruses, polioviruses, coxsackieviruses of the A and B groups, echo virus and Mengo virus. Such compounds are also useful as intermediates for preparing additional benzimidazole antiviral compounds.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: August 13, 1996
    Assignee: Eli Lilly and Company
    Inventors: Shawn C. Miller, Frantz Victor, Wayne A. Spitzer, Thomas R. Sattelberg, Sr., Mark J. Tebbe
  • Patent number: 5541204
    Abstract: Compounds of the formula ##STR1## and pharmaceutically acceptable salts thereof wherein: R.sup.1 to R.sup.9 are as defined herein and m is the integer 0 or 1. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity, gastrointestinal diseases and achalasia.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: July 30, 1996
    Assignee: Bristol-Myers Squibb Company
    Inventors: Philip M. Sher, William N. Washburn, Kathleen M. Poss
  • Patent number: 5534535
    Abstract: Antiviral nucleoside analogues contain a substituted benzimidazole base attached to a carbocyclic ring in place of the conventional sugar residue. Particularly preferred compounds include those in which the 2-, 5- and 6- positions of the benzimidazole base are substituted by halogen. The compounds have activity against herpes virus especially cytomegalovirus and also hepatitis B virus infections.
    Type: Grant
    Filed: September 9, 1994
    Date of Patent: July 9, 1996
    Assignees: Burroughs Wellcome Co., The Regents of the University of Michigan
    Inventors: Leroy B. Townsend, John C. Drach, Steven S. Good, Susan M. Daluge, Michael T. Martin
  • Patent number: 5534534
    Abstract: A pharmaceutical composition for oral use comprising an effective amount of a compound of the formula (I) having antagonistic action to angiotensin II ##STR1## (wherein the ring W is an optionally substituted N-containing heterocyclic residue; R.sup.3 is a group capable of forming an anion or a group convertible thereinto; X is a direct bond or a spacer having an atomic length of two or less between the phenylene group and the phenyl group; and n is an integer of 1 or 2) and an oily substance having a lower melting point, and a method for preparing a pharmaceutical composition for oral use comprising an effective amount of a compound of the formula (I) and an oily substance having a lower melting point, which comprises admixing the compound of the formula (I) with an oily substance having a lower melting point and then subjecting the mixture to molding.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: July 9, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Tadashi Makino, Yashio Mizukami, Jun-ichi Kikuta
  • Patent number: 5532262
    Abstract: There are described new active compound combinations of a compound of the formula (I) ##STR1## with known fungicidal active compounds, and their use for the control of phytopathogenic fungi.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: July 2, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Brandes, Heinz-Wilhelm Dehne, Stefan Dutzmann, Karl-Heinz Kuck, Bernd-Wieland Kruger
  • Patent number: 5521204
    Abstract: This invention is directed to certain 2-(alkoxycarbonylamino)- and 2-(alkoxycarbonylimino)benzlmidazole derivatives which are useful in the topical, oral or parenteral treatment of animals suffering from helminth infections.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 28, 1996
    Assignee: Pfizer Inc.
    Inventors: Bernard J. Banks, Christopher J. Dutton, Alexander C. Goudie
  • Patent number: 5491161
    Abstract: Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives having the formula ##STR1## wherein n is 0 or 1;R.sup.1 is hydrogen, nitro, amino, mono- or di(C.sub.1-6 alkyl)amino, halo, C.sub.1-6 alkyl, hydroxy or C.sub.1-6 alkyloxy;R.sup.2 is hydrogen; C.sub.1-10 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 alkynyl; C.sub.3-7 cycloalkyl; phenyl; substituted phenyl; C.sub.1-4 alkyl substituted with phenyl, substituted phenyl, naphthalenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, C.sub.3-7 cycloalkyl; andR.sup.3 is hydrogen; C.sub.1-8 alkyl; C.sub.3-7 cycloalkyl; hydroxy; amino; C.sub.1-6 alkyloxy; C.sub.1-6 alkyloxycarbonylamino; phenyl; C.sub.1-4 alkyl substituted with phenyl, piperazinyl, 4-(C.sub.1-4 alkyl)piperazinyl or morpholinyl;each substituted phenyl independently is phenyl substituted with a substituent independently selected from halo, hydroxy, hydroxymethyl, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: February 13, 1996
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Marcel A. C. Janssen, Alfons H. M. Raeymaekers, Eddy J. E. Freyne, Michael N. Greco
  • Patent number: 5457102
    Abstract: Pyrroloimidazolyl and imidazopyridinyl substituted 1H-benzimidazole derivatives having the formula ##STR1## wherein n is 0 or 1;R.sup.1 is hydrogen, nitro, amino, mono- or di(C.sub.1-6 alkyl)amino, halo, C.sub.1-6 alkyl, hydroxy or C.sub.1-6 alkyloxy;R.sup.2 is hydrogen; C.sub.1-10 alkyl; C.sub.3-6 alkenyl; C.sub.3-6 alkynyl; C.sub.3-7 cycloalkyl; phenyl; substituted phenyl; C.sub.1-4 alkyl substituted with phenyl, substituted phenyl, naphthalenyl, thienyl, furanyl, C.sub.1-4 alkylfuranyl, C.sub.3-7 cycloalkyl; andR.sup.3 is hydrogen; C.sub.1-8 alkyl; C.sub.3-7 cycloalkyl; hydroxy; amino; C.sub.1-6 alkyloxy; C.sub.1-6 alkyloxycarbonylamino; phenyl; C.sub.1-4 alkyl substituted with phenyl, piperazinyl, 4-(C.sub.1-4 alkyl)piperazinyl or morpholinyl;each substituted phenyl independently is phenyl substituted with a substituent independently selected from halo, hydroxy, hydroxymethyl, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, C.sub.
    Type: Grant
    Filed: July 7, 1994
    Date of Patent: October 10, 1995
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Marcel A. C. Janssen, Alfons H. M. Raeymaekers, Eddy J. E. Freyne, Michael N. Greco
  • Patent number: 5441969
    Abstract: The present invention discloses compounds of the formula ##STR1## or a pharmaceutically-acceptable addition salt thereof whereinR' and R" independently of each other are hydrogen or alkyl, or R' and R" together form a 3 to 6 membered alkylene chain;one of R.sup.1 and R.sup.2 is aryl which may be substituted one or more times with halogen, CF.sub.3, CN, OH, alkyl, cycloalkylalkyl, alkenyl, alkynyl, alkoxy, amino, nitro, sulphamoyl, tetrazolyl, CO.sub.2 H, CO.sub.2 -alkyl and the other of R.sup.1 and R.sup.2 is hydrogen, halogen, alkoxy, amino or alkyl; andR.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of each other are hydrogen, halogen, amino, nitro, CN, OH, CF.sub.3, alkyl or alkoxy; and n is 0 or 1; provided that neither of R.sup.1 and R.sup.2 is phenyl or substituted phenyl when n is 0.The compounds are useful as pharmaceuticals, for example, in the treatment of ischemia, anoxia, migraine and psychosis.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: August 15, 1995
    Assignee: NeuroSearch A/S
    Inventors: Oskar Axelsson, Dan Peters, Elsebet O Nielsen
  • Patent number: 5432187
    Abstract: The present inventions relates to the use of certain benzimidazole compounds in the treatment of diseases caused by microsporidia organisms, in particular the treatment of diarrhea in patients infected with human immunodeficiency virus.
    Type: Grant
    Filed: September 15, 1993
    Date of Patent: July 11, 1995
    Assignee: SmithKline Beecham, p.l.c.
    Inventor: Brian G. Gazzard
  • Patent number: 5369128
    Abstract: The invention provides a method of synchronizing farrowing in swine comprising the steps of administering an effective amount of a prostaglandin and then administering to the sows an effective amount of a peripheral .alpha..sub.2 adrenergic agonist, such that farrowing is induced.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: November 29, 1994
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Walter H. Hsu
  • Patent number: 5346704
    Abstract: This invention provides a dry pulverulent composition which is comprised of (1) a particulated agrochemical ingredient such as a herbicide; and (2) an inorganic salt ingredient such as sodium, potassium or ammonium bicarbonate or a mixture thereof, which is adsorbed on the surface of the agrochemical particles. The agrochemical ingredient can be a mixture of two or more biologically active organic compounds. The adsorbed inorganic salt ingredient also can be in a blend with a water-soluble or water-dispersible organic polymer ingredient as a film coating, and the coating of ingredients can function as a slow-release medium in the presence of moisture.
    Type: Grant
    Filed: August 11, 1993
    Date of Patent: September 13, 1994
    Assignee: Church & Dwight Co., Inc.
    Inventor: M. Stephen Lajoie
  • Patent number: 5338551
    Abstract: This invention provides a dry pulverulent composition which is comprised of (1) a particulated agrochemical ingredient such as a herbicide; and (2) an inorganic salt ingredient such as sodium, potassium or ammonium bicarbonate or a mixture thereof, which is adsorbed on the surface of the agrochemical particles. The agrochemical ingredient can be a mixture of two or more biologically active organic compounds. The adsorbed inorganic salt ingredient also can be in a blend with a water-soluble or water-dispersible organic polymer ingredient as a film coating, and the coating of ingredients can function as a slow-release medium in the presence of moisture.
    Type: Grant
    Filed: July 2, 1992
    Date of Patent: August 16, 1994
    Inventor: M. Stephen Lajoie
  • Patent number: 5326777
    Abstract: Microbicidal synergistic combinations of active compounds composed of known azol and benzimidazole derivatives are described, as is their use in the protection of materials.
    Type: Grant
    Filed: July 1, 1992
    Date of Patent: July 5, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Georg-Wilhelm Ludwig, Otto Exner, Hans-Georg Schmitt, Karl-Heinz Buchel, Graham Holmwood
  • Patent number: 5314903
    Abstract: The present invention discloses compounds of the formula ##STR1## wherein R' and R" independently of each other are hydrogen or alkyl, or R' and R" together form a 3 to 6 membered alkylene chain;n is 1 or 2;R.sup.1 is phenyl which may be substituted one or more times with halogen, CF.sub.3, alkoxy, alkyl, or amino; andR.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of each other are hydrogen, halogen, amino, CF.sub.3, alkyl or alkoxy; or a pharmaceutically-acceptable addition salt thereof.The compounds are useful as pharmaceuticals, for example, in the treatment of ischemia, anoxia, migraine and psychosis.
    Type: Grant
    Filed: November 18, 1992
    Date of Patent: May 24, 1994
    Assignee: NeuroSearch A/S
    Inventors: Oskar Axelsson, Mikkel Thaning, Peter Moldt
  • Patent number: 5256681
    Abstract: [5(6)-(benzisoxa-, benzisothia- or indazol-3-yl)-1H-benzimidazol-2-yl]carbamates of formula (I) wherein R.sup.1 is hydrogen, C.sub.1-4 alkyl, halo, hydroxy or C.sub.1-4 alkyloxy; R.sup.2 is C.sub.1-4 alkyl; and X is O, S, SO, SO.sub.2 or NR.sup.3, said R.sup.3 being hydrogen, C.sub.1-4 alkyl, aryl or arylC.sub.1-4 alkyl. The compounds of formula (I) have anthelminthic properties. Compositions containing said compounds as active ingredient, a method of combating helminths, and a process for preparing said compounds and compositions.
    Type: Grant
    Filed: August 27, 1991
    Date of Patent: October 26, 1993
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Alfons H. M. Raeymaekers, Eddy J. E. Freyne, Gustaaf M. Boeckx
  • Patent number: 5240940
    Abstract: Fungicidal compositions comprise a combination of two fungicides, one of which is a quinoline or cinnoline compound of the formula (1) ##STR1## the substituents being as described in the specification.
    Type: Grant
    Filed: May 12, 1992
    Date of Patent: August 31, 1993
    Assignee: DowElanco
    Inventors: Wendell R. Arnold, Michael J. Coghlan, Glen P. Jourdan, Eriks V. Krumkalns, Robert G. Suhr
  • Patent number: 5210091
    Abstract: The application discloses benzimidazole derivatives, pharmaceutical preparations comprised the compounds, their preparation and use in the treatment of disorders of the Central Nervous System such as ischemia, migraine, epilepsia, psychosis, Parkinsonism and depression.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: May 11, 1993
    Assignee: NeuroSearch A/S
    Inventors: Oskar Axelsson, Mikkel Thaning, Peter Moldt
  • Patent number: 5200422
    Abstract: A compound having the formula ##STR1## wherein R.sup.1 is hydrogen, NH.sub.2 or C.sub.1-6 -alkyl which may be branched;X is O, S, NCN;Y is O, S;R.sup.4, R.sup.5, R.sup.6 and R.sup.7 independently of each other are hydrogen, halogen, CF.sub.3, NO.sub.2, NH.sub.2, OH, C.sub.1-6 -alkoxy, C(.dbd.O)-phenyl or SO.sub.2 NR.sup.I R.sup.II wherein R.sup.I and R.sup.II independently are hydrogen or C.sub.1-6 -alkyl;R.sup.11 is hydrogen, halogen, NO.sub.2 or SO.sub.2 NR'R" wherein R' and R" independently are hydrogen or C.sub.1-6 -alkyl;R.sup.13 is hydrogen, halogen, phenyl, CF.sub.3, NO.sub.2 ;R.sup.12 is hydrogen or together with R.sup.13 forms a C.sub.4-7 -carbocyclic ring which may be aromatic or partially saturated;R.sup.14 is hydrogen or together with R.sup.13 forms a C.sub.
    Type: Grant
    Filed: July 17, 1991
    Date of Patent: April 6, 1993
    Assignee: NeuroSearch A/S
    Inventors: Soren-Peter Olesen, Frank Watjen
  • Patent number: 5190932
    Abstract: The invention relates to the use of water-soluble polymers containing chemically bonded tertiary and/or quaternary ammonium groups as auxiliaries for formulating microbicides, the microbicide formulations prepared using these water-soluble polymers and the use of these formulations for preserving industrial materials.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: March 2, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Dhein, Lothar Backer, Otto Exner, Walter Radt, Ingrid Radt, Christian Radt, Hans G. Schmitt
  • Patent number: 5185357
    Abstract: An antifungal composition made up of at least one compound represented by the formula (I): ##STR1## wherein X represents a group of the formula --NHCOOR in which R is --CH.sub.3 or --C.sub.2 H.sub.5, or 4-thiazolyl group and at least one compound represented by the formula (II): ##STR2## wherein Y represents hydrogen or halogen, Z represents halogen and R represents alkyl group of 1 to 8 carbon atoms. The composition preferably comprises 10 to 90% by weight of the compound(s) of formula (I).
    Type: Grant
    Filed: February 21, 1991
    Date of Patent: February 9, 1993
    Assignee: Shinto Paint Co., Ltd.
    Inventor: Keiichiro Inui
  • Patent number: 5179116
    Abstract: A wood preservative which is based on a dimethylalkylamine and an acid and contains dimethylalkylamine, a water-soluble acid and a water-insoluble acid and/or 2-(methoxycarbonylamino)-benzimidazole is used for preserving wood.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: January 12, 1993
    Assignee: Dr. Wolman GmbH
    Inventors: Reimer Goettsche, Hans-Volker Borck, Hans-Norbert Marx
  • Patent number: 5149700
    Abstract: This invention relates to substituted arylsulfonamides and benzamides possessing aniarrhythmic activity, to pharmaceutical compositions and to methods for production thereof.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: September 22, 1992
    Assignee: American Home Products Corporation
    Inventors: John W. Ellingboe, Jehan F. Bagli, Michael W. Winkley
  • Patent number: 5147887
    Abstract: A fungicidal composition comprising a fungicidally effective amount of (i) a substituted 1-hydroxyethyl-triazole of the formula ##STR1## in which A is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--, or an addition product thereof with an acid or metal salt, and (ii) at least one member selected from the group consisting ofA) wettable sulphur,B) a polyhalogenoalkylthio derivative,C) a quanidine derivative,D) an aromatic carboxylic acid derivative,E) a dithiocarbamate,F) a benzimidazole derivative,G) an imidazole or triazole derivative,H) a phosphoric acid ester,I) a tetrahydroquinoline derivative,J) an S,N-heterocyclene compound,K) a urea derivative,L) a sulphonamide derivative,M) a polyhydroxy ether derivative,N) a triazine derivative,O) a copper complex salt,P) an N-formyl derivative,Q) a morpholine derivative,R) a quinoxaline derivative, andS) a dicarboximide derivative.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: September 15, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Brandes, Gerd Hanssler, Paul Reinecke, Hans Scheinpflug, Graham Holmwood
  • Patent number: 5135928
    Abstract: This invention relates to novel triazolo derivatives, a process for the preparation thereof, pharmaceutical compositions comprising the same, to the use of the said triazolo derivatives for the treatment of diseases and also for the preparation of pharmaceutical compositions suitable for the treatment of the said diseases.The new triazolo derivatives of the general formulae (Ia) and (Ib), ##STR1## wherein Q represents hydrogen or a heterocyclic group optionally bearing one or more C.sub.1-4 alkyl substituent(s); or a group of the formula SR.sup.1, whereinR.sup.1 stands for straight or branched chained C.sub.1-4 alkyl or phenyl-(C.sub.1-4 alkyl); or q represents a group of the formula NR.sup.2 R.sup.3, whereinR.sup.2 and R.sup.3 each represent hydrogen, straight or branched chain C.sub.1-12 alkyl, C.sub.2-6 alkenyl or phenyl-(C.sub.1-4 alkyl);R.sup.4 and R.sup.7 each represent hydrogen, C.sub.1-6 alkyl or phenyl-(C.sub.1-4 alkyl) optionally bearing one or more halogen substituent(s);R.sup.5 and R.sup.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: August 4, 1992
    Assignee: Egis Gyogyszergyar
    Inventors: Jozsef Reiter, Jozsef Barkoczy, Lujza Petocz, Frigyes Gorgenyi, Marton Fekete, Eniko Szirt nee Kiszelly, Gabor Gigler, Istvan Gacsalyi, Istvan Gyertyan, Klara Reiter nee Esses
  • Patent number: 5106857
    Abstract: A method of treating cardiac arrhythmias and muscle tension and spasticity with N-(1-methyl-3-pyrrolidinyl)-1-(phenylmethyl)-1H-benzimidazol-2-amine and analogs and the pharmaceutical compositions are herein disclosed. Illustratively, the compound having the structure: ##STR1## corrects an induced arrhythmia in 7 out of 8 dogs at 7 mg/kg IV and has an ED.sub.50 of 21 mg/kg in the mouse Straub-tail test.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: April 21, 1992
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Albert D. Cale, Jr., Thomas W. Gero
  • Patent number: 5043338
    Abstract: The invention relates to synergistic combinations of known fungicide active ingredients and their application in plant protection.
    Type: Grant
    Filed: May 21, 1990
    Date of Patent: August 27, 1991
    Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara, R.T.
    Inventors: Tamas Detre, Lajos Rejto, Jozsef Sos, Andras Szego, Erzsebet Schuszler, Sandor ngyan, Katalin Keller Nee Marmarosi, Horst Lyr, Dieter Zanke, Brita Lenner, Marlies Strump, Gyula Oros, Ferenc Viranyi, Tibor rsek, Gyongyver Nagy, Laszlo Hornok, Attila Molnar
  • Patent number: 5039691
    Abstract: Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: ##STR1## wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring;R.sub.1 and R.sub.2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C.sub.3 -C.sub.6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy;R.sub.3, R.sub.4 and R.sub.5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R.sub.4 and R.sub.5 or R.sub.3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R.sub.1 and R.sub.2 substituted benzyl or phenyl.R.sub.
    Type: Grant
    Filed: May 8, 1990
    Date of Patent: August 13, 1991
    Assignee: Marion Merrell Dow Inc.
    Inventors: Ciro J. Spagnuolo, Carl Kaiser, Theodore Adams
  • Patent number: 4988693
    Abstract: The invention relates to synergistic combinations of known fungicide active ingredients and their application in plant protection.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: January 29, 1991
    Assignee: Chinoin Gyogyszer- Es Vegyeszeti Termekek Gyara, R. T.
    Inventors: Tamas Detre, Lajos Rejto, Jozsef Sos, Andras Szego, Ferenc Viranyi, Tibor rsek, Gyongyver Nagy nee Hegyi, Laszlo Hornok, Attila Molnar, Erzsebet Schuszler, Sandor ngyan, Katalin Marmarosi, nee Kellner, Lyr Horst, Dieter Zanke, Brita Lenner, Marlies Strump, Gyula Oros
  • Patent number: 4980346
    Abstract: The invention relates to synergistic fungicidal and acaricidal compositions containing two or three active ingredients in a ratio of 10:1-1:10 and 20:1:1-1:10:10, selected from the group of N-alkyl(ene)-N-(0,0-disubstituted-thiophosphoryl)-N', N'-substituted glycine amide derivatives, Triforine, Carbendazim, copper-oxyquinolate, cycloheximide, Mancozeb, benzimidazole derivatives, phenyl amide derivatives F-849, Folpet, Captofol, Iprodione or S-39475.
    Type: Grant
    Filed: January 11, 1989
    Date of Patent: December 25, 1990
    Assignee: Eszakmagyarorsuagi Vegyimuvek
    Inventors: Karoly Balogh, Marta Bartha nee Kocsis, Zsuzsa Dancs nee Rozsnyai, Erzsebet Grega nee Toth, Magdolna Magyar nee Tomorkenyi, Istvan Nagy, Jozsef Nagy, Gyongyver S. Nagy nee Hegyi, Gyula Oros, Csaba Pavliscsak, Karoly Pasztor, Gyula Tarpai, Eszter Urszin nee Simon
  • Patent number: 4940722
    Abstract: A seed disinfectant composition comprising(A) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-pente n-3-ol and(B) At least one benzimidazole thiophanate fungicide and optionally comprising(C) O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)phosphorothioate and/or(D) 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid or a salt thereof are disclosed. The seed disinfectant composition of the present invention exhibits a synergistically high preventing effect on various seed born diseases and simultaneously has a wide antifungal spectrum and shows a stable preventing effect on the fungi having resistance to conventional disinfectants.
    Type: Grant
    Filed: November 17, 1987
    Date of Patent: July 10, 1990
    Assignee: Sumitomo Chemical Companmy, Limited
    Inventor: Hirotaka Takano
  • Patent number: 4906653
    Abstract: A method for controlling molluscs with 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate of the formula ##STR1## and molluscicides containing a mixture of 2-(2-chloro-1-methoxyethoxy)phenyl methylcarbamate with methyl benzimidazol-2-ylcarbamate is described.
    Type: Grant
    Filed: February 10, 1988
    Date of Patent: March 6, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Kiehs, Christoph Kuenast
  • Patent number: 4874759
    Abstract: Hydroxyindole-3-carboxylic acid amide compounds of the general formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, the same or different, respectively a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a heteroaryl group, or R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 are respectively groups which are combined to each other taken together with the adjacent nitrogen atom to form a heterocyclic group, R.sup.5 is an alkyl group, R.sup.6 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group and X is a hydrogen atom, a halogen atom or a lower alkanoyl group, or their acid addition salts.These compounds are of use as diuretics or a therapeutic medicine for circulation system diseases.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: October 17, 1989
    Assignee: Yoshitomi Pharmaceutical Industries, Ltd.
    Inventors: Tetsuya Tahara, Tsuguo Ikebe, Ichiro Hakamada, Osamu Yaoka
  • Patent number: 4859689
    Abstract: There is disclosed a fungicidal composition comprising (A) a fungicidal compound selected from the group consisting of (i) benzimidazole compounds of the formula ##STR1## wherein W is H, or alkyl carbamoyl; Y is thiazolyl, dihydrothiazolyl, tetrahydrothiazolyl or furyl; Z is H, halogen or alkyl and (ii) benzimidazole related compounds of the formula ##STR2## wherein R.sub.3 is C.sub.1-2 alkyl, and Z is as defined above, and (B) a synergist alkyl pyridinium salt of the formula ##STR3## wherein R is an alkyl containing 8 to 20 carbon atoms; and X is a monovalent anion.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: August 22, 1989
    Assignee: Safer, Inc.
    Inventors: George S. Puritch, Edward S. Kondo
  • Patent number: 4857541
    Abstract: A fungicide which is particularly effective against benomyl resistant fungi is selected from the group of fungicides represented by the formula: ##STR1## wherein R is C.sub.n H.sub.2n+1 and n is 1, 2, 3 or 6 or R is phenyl. The method comprises applying as a suspension an effective amount of the one or more fungicides selected from the formula to benomyl resistant fungi, such as benomyl resistant isolates of Botrytis cinerea.
    Type: Grant
    Filed: August 7, 1986
    Date of Patent: August 15, 1989
    Assignee: Canadian Patents and Development Limited/Societe Canadienne Des Brevets et D'Exploitation Limitee
    Inventor: Mikio Chiba
  • Patent number: 4843090
    Abstract: A controlling composition for Fusarium diseases caused by the benzimidazole-resistant or sensitive strain of Fusarium which comprises as an active ingredient a benzimidazole derivative represented by the general formula (I) (hereinafter referred to as present composition), ##STR1## wherein R represents a C.sub.1 -C.sub.3 lower alkyl group, and n represents 1, 2 or 3.
    Type: Grant
    Filed: September 8, 1988
    Date of Patent: June 27, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroki Tomioka, Tadashi Ooishi, Naonori Hirata
  • Patent number: 4831032
    Abstract: The present invention provides benzimidazoles of the general formula: ##STR1## wherein R.sub.1, X, A, and R.sub.2 are as defined in the specification. The present invention also provides processes for the preparation of these new benzimidazoles and pharmaceutical compositions containing them, as well as intermediates for the preparation thereof.The new benzimidazoles are useful to treat heart or circulatory diseases which respond to a lowering of blood pressure, a positive inotropic action and/or an improvement in microcirculation.
    Type: Grant
    Filed: July 3, 1986
    Date of Patent: May 16, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein
  • Patent number: 4826862
    Abstract: Novel [(5(6) (1H-azole-1-ylmethyl)benzimidazole]carbamates derivatives having anthelminthic properties, compositions containing these compounds as active ingredient, and a method for combating the growth of helminths.
    Type: Grant
    Filed: February 12, 1988
    Date of Patent: May 2, 1989
    Assignee: Janssen Pharmaceutica, N.V.
    Inventors: Alfons H. M. Raeymaekers, Eddy J. E. Freyne
  • Patent number: 4745125
    Abstract: Antiulcer amino-benzimidazole compounds substituted on the nitrogen; these compounds correspond to the following general formula: ##STR1## in which the various substituents are defined hereinbelow.
    Type: Grant
    Filed: January 20, 1987
    Date of Patent: May 17, 1988
    Assignee: Novapharme
    Inventors: Jacques N. Astoin, Bernard Hublot, Francis Lepage
  • Patent number: 4737510
    Abstract: Novel bioactive metabolites from the Caribbean sponge Agelas coniferin are disclosed. These compounds are generically referred to as halopyrroles. They exhibit antiviral and antibacterial properties, and, thus, are useful for various non-therapeutic and therapeutic purposes.
    Type: Grant
    Filed: September 30, 1986
    Date of Patent: April 12, 1988
    Assignee: The Board of Trustees of The University of Illinois
    Inventor: Kenneth L. Rinehart, Jr.
  • Patent number: 4730003
    Abstract: The present invention provides compounds of the general formula: ##STR1## wherein the various substituents are defined hereinbelow. The compounds are used for the treatment and/or prophylaxis of heart and circulatory diseases.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: March 8, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann
  • Patent number: 4721717
    Abstract: The present invention provides aminoalcohols of the general formula: ##STR1## wherein R.sub.1 and R.sub.2, which can be same or different, are hydrogen atoms, hydroxyl groups, C.sub.1 -C.sub.4 -alkoxy, benzyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkanesulphonylamino, C.sub.1 -C.sub.4 -alkanesulphinyl or C.sub.1 -C.sub.4 -alkanesulphonyl radicals, m is 2, 3 or 4, X and Y, which can be the same or different, are hydrogen atoms or benzyl radicals and R.sub.3 is a phenyl radical substituted twice by C.sub.1 -C.sub.6 -alkyl radicals, a nitrophenyl radical, an aminophenyl radical, a 1,3,5-tri-C.sub.1 -C.sub.6 -alkyl-2,4-dioxo-1H,3H-pyrimidin-6-yl radical, an indolyl radical, an indazolyl radical, a benzimidazolyl radical, a 1,4-di-C.sub.1 -C.sub.6 -alkylpyrazol-5-yl radical or a radical of the general formula: ##STR2## wherein R.sub.4 and R.sub.5, which can be the same or different, are C.sub.1 -C.sub.4 -alkyl radicals and R.sub.6 is a C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: January 26, 1988
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Wolfgang Kampe, Erwin Bohm, Klaus Strein
  • Patent number: 4618620
    Abstract: A fungicidal composition which comprises an inert carrier and as an active ingredient (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3- ol and a benzimidazole-thiophanate type fungicide in the ratio of 1 to 0.1 to 10 by part by weight in a total amount of 0.1 to 99.9% by weight.
    Type: Grant
    Filed: August 14, 1985
    Date of Patent: October 21, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukio Ishiguri, Hirotaka Takano, Yuji Funaki