Tetrazines Patents (Class 544/179)
  • Patent number: 5274091
    Abstract: 3-Amino-6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (ADMPT) and a method of making it.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: December 28, 1993
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Michael D. Coburn, Donald G. Ott
  • Patent number: 5260291
    Abstract: [ 3H]-Imidazo[ 5,1-d] -1,2,3,5-tetrazin-4-one derivatives of the formula: ##STR1## wherein R.sup.1 represents hydrogen, or an alkyl, alkenyl or alkynyl group containing up to 6 carbon atoms, each such group being unsubstituted or substituted by from one to three substituents selected from halogen atoms, alkoxy, alkylthio, alkylsulphinyl and alkylsulphonyl groups containing up to 4 carbon atoms, and optionally substituted phenyl groups, or R.sup.1 represents a cycloalkyl group containing from 3 to 8 carbon atoms, and R.sup.2 represents a carbamoyl group optionally N-substituted by one or two groups selected ftom alkyl and alkenyl groups containing up to 4 carbon atoms, and cycloalkyl groups containing 3 to 8 carbon atoms, are new therapeutically useful compounds possessing antineoplastic and immunomodulatory activity.
    Type: Grant
    Filed: October 18, 1991
    Date of Patent: November 9, 1993
    Assignee: Cancer Research Campaign Technology Limited
    Inventors: Edward Lunt, Malcolm F. G. Stevens, Robert Stone, Kenneth R. H. Wooldridge, Edward S. Newlands
  • Patent number: 5250528
    Abstract: This invention relates to new aminopiperazine derivatives having the potentiation of the cholinergic activity and represented by the general formula [I]: ##STR1## wherein R.sup.1 is lower alkyl, aryl, ar(lower)alkoxy or a heterocyclic group, each of which may be substituted with halogen,R.sup.2 is hydrogen or lower alkyl,R.sup.3 is cyclo(lower)alkyl, aryl or ar(lower)-alkyl, each of which may be substituted with halogen,A is ##STR2## or lower alkylene, and Y is ##STR3## and pharmaceutically acceptable salts thereof, to processes for the preparation thereof and to a pharmaceutical composition comprising the same.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: October 5, 1993
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Teruo Oku, Eishiro Todo, Yoshihiro Yokota, Hiroshi Kayakiri, Masashi Hashimoto
  • Patent number: 5200116
    Abstract: Described are a series of novel photochromic benzopyran and naphthopyran compounds substituted with (1) a cyclopropyl group and (2) a phenyl, substituted phenyl, or 5-member aromatic heterocyclic group at the 2-position of the benzopyran or naphthopyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic or plano lenses that incorporate the novel pyran compounds or combinations of the novel pyran compounds with other complementary photochromic compounds are described.
    Type: Grant
    Filed: July 23, 1990
    Date of Patent: April 6, 1993
    Assignee: PPG Industries, Inc.
    Inventor: Harry G. Heller
  • Patent number: 5187274
    Abstract: In a process to avoid the formation of waste water in the production of hexamine from ammonia and the stream of gas containing formaldehyde resulting from the catalytic oxidation of methanol on metallic oxide catalysts, or by oxidative dehydrogenation to formaldehyde, the liquid volume during reaction for the production of hexamine is kept constant, and carbon monoxide, the organic components of the exhaust gas and also hydrogen, if present, are oxidized to carbon dioxide and water, thus avoiding an energy-consuming condensation of the condensable components from the stream of exhaust gas and their treatment.
    Type: Grant
    Filed: July 19, 1991
    Date of Patent: February 16, 1993
    Assignee: Josef Meissner GmbH & Co.
    Inventors: Heinrich Hermann, Gunther Pelster, Klaus Degener
  • Patent number: 5158954
    Abstract: Fungicidal compounds of the formula (I): ##STR1## and stereoisomers thereof, wherein K is oxygen or sulphur; Z is optionally substituted aryl or optionally substituted heteroaryl; X is O, S(O).sub.n, NR.sup.4, CR.sup.1 R.sup.2, CHR.sup.5, CO, CR.sup.1 (OR.sup.2), C.dbd.CR.sup.1 R.sup.2, CHR.sup.1 CHR.sup.2, CR.sup.1 .dbd.CR.sup.2, CHR.sup.1 CR.sup.2 .dbd.CH, C.dbd.C, OCHR.sup.1, CHR.sup.1 O, OCHR.sup.1 O, S(O).sub.n CHR.sup.1, S(O).sub.n CHR.sup.1 O, CHR.sup.1 S(O).sub.n, CHR.sup.1 OSO.sub.2, NR.sup.4 CHR.sup.1, CHR.sup.1 NR.sup.4, CO.sub.2, O.sub.2 C, SO.sub.2 O, OSO.sub.2, CO.CO, COCHR.sup.1, COCHR.sup.1 O, CHR.sup.1 CO, CHOH.CHR.sup.1, CHR.sup.1.CHOH, ##STR2## CONR.sup.4, OCONR.sup.4, NR.sup.4 CO, CSNR.sup.4, OCS.NR.sup.4, SCO.NR.sup.4, NR.sup.4 CO.sub.2, NR.sup.4 CS, NR.sup.4 CSO, NR.sup.4 COS, NR.sup.4 CONR.sup.4, S(O).sub.n NR.sup.4, NR.sup.4 S(O).sub.n, CS.sub.2, S.sub.2 C, CO.S, SCO, N.dbd.N, N.dbd.CR.sup.1, CR.sup.1 .dbd.N, CHR.sup.1 CHR.sup.2 CH(OH), CHR.sup.1 OCO, CHR.sup.1 SCO, CHR.sup.1 NR.sup.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: October 27, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: John M. Clough, Christopher R. A. Godfrey, Stephen P. Heaney, Kenneth Anderton
  • Patent number: 5158959
    Abstract: What are disclosed are aminoacid compounds of the formula ##STR1## wherein n is 0 or 1, and salts thereof, said compounds and salts having hypotensive properties; methods for making the compounds; pharmaceutical compositions containing the compounds or salts; and use of the compounds and salts for treating hypertension.
    Type: Grant
    Filed: December 27, 1983
    Date of Patent: October 27, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rolf Geiger, Volker Teetz, Hansjorg Urbach, Bernward Scholkens, Rainer Henning
  • Patent number: 5145954
    Abstract: Compounds of formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 and R.sup.2, which are the same or different, are optionally substituted alkyl; W, X, Y and Z, which are the same or different, are hydrogen, halogen, hydroxy, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted aryloxyalkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted alkynyl, optionally substituted amino, optionally substituted arylazo, optionally substituted heteroarylalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted acylamino, nitro, cyano, --OR.sup.3, --SR.sup.3, --CO.sub.2 R.sup.4, --CONR.sup.5 R.sup.6, --COR.sup.7, --CR.sup.8 .dbd.NR.sup.9, --N.dbd.CR.sup.10 R.sup.11, --SOR.sup.12 or --SO.sub.2 R.sup.
    Type: Grant
    Filed: April 17, 1989
    Date of Patent: September 8, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul DeFraine, Christopher R. A. Godfrey, Thomas E. Wiggins, David J. Tapolczay
  • Patent number: 5138064
    Abstract: Novel 3-pyrrolidinylthio-1-azabiycyclo[3.2.0]hept-2-ene-2-carboxylic acid compounds and pharmaceutically acceptable salts thereof have antimicrobial activity and are useful as medicaments in the treatment of infectious diseases caused by pathogenic microorganisms.
    Type: Grant
    Filed: February 6, 1990
    Date of Patent: August 11, 1992
    Assignee: Fujisawa Pharmaceutical Company, Ltd.
    Inventors: Masayoshi Murata, Hideo Tsutsumi, Keiji Matsuda, Kohji Hattori, Takashi Nakajima
  • Patent number: 5112817
    Abstract: Novel heterocyclic compounds, which are represented by the following general formula, useful as anticancer drug potentiaters having a potentiating effect on the incorporation of anticancer drugs into cancer cells, the compounds each synthesized by, for example, reacting a epoxy compound obtained by reacting a heterocyclic compound with an epihalogenohydrin, with an amine derivative.
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: May 12, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Nobuyuki Fukazawa, Makoto Odate, Tsuneji Suzuki, Kengo Otsuka, Takashi Tsuruo, Wakao Sato
  • Patent number: 5087726
    Abstract: This invention relates to novel compounds which are ACAT inhibitors rendering them useful in lowering blood cholesterol levels. The compounds are carbamates represented by the general formula ##STR1## wherein Ar and Ar' represent phenyl or naphthyl each of which may be substituted; m and n each represent zero or one; Z and Y are hydrogen, aliphatic hydrocarbon, heterocyclic, aryl or carbocyclic containing groups.
    Type: Grant
    Filed: February 13, 1990
    Date of Patent: February 11, 1992
    Assignee: Warner-Lambert Company
    Inventors: Patrick M. O'Brien, Drago R. Sliskovic
  • Patent number: 5053073
    Abstract: Compounds of formula (I): ##STR1## and stereoisomers thereof, wherein W is R.sup.1 O.sub.2 C--C.dbd.CH--ZR.sup.2, wherein R.sup.1 and R.sup.2, which are the same or different, are alkyl or fluoroalkyl groups, and Z is either an oxygen or sulphur atom; A is an oxygen or sulphur atom, --NR.sup.3 --, or --CR.sup.4 R.sup.5 --; X, Y and Z.sup.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: October 1, 1991
    Assignee: Imperial Chemical Industries PLC
    Inventors: Vivienne M. Anthony, John M. Clough, Paul deFraine, Christopher R. A. Godfrey, Kevin Beautement
  • Patent number: 5017212
    Abstract: A compound of the general formula: ##STR1## wherein Q is a condensed heterocyclic group having an N atom in the bridgehead which may be substituted, W is O or S, R.sub.1 and R.sub.2 each are an alkyl group, an alkoxy group or halogen and Z is CH or N, and a salt thereof, which is useful as a herbicide.
    Type: Grant
    Filed: March 17, 1987
    Date of Patent: May 21, 1991
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yasuo Ishida, Kazunari Ohta, Tatsuo Nakahama, Harutoshi Yoshikawa
  • Patent number: 5001138
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: March 19, 1991
    Assignee: Nihon Tokushu Noyaku Seizo, K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4968796
    Abstract: Disclosed is a process for the preparation of a sulphonylisothiourea of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, and Z are as defined herein, which comprises reacting a sulphonic acid amide of the formulaR.sup.1 --SO.sub.2 --NH.sub.2, (II)or a metal salt thereof, with an N-heteroaryl-iminodithiocarbonic acid S,S-diester of the formula ##STR2## at a temperature between about 20.degree. C. and 200.degree. C. Intermediates and a process for their preparation are also disclosed.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Jochem Riebel
  • Patent number: 4968676
    Abstract: Cyclohexylamines of the formula ##STR1## where X is a single bond or an alkylene chain, Y is hydrogen or an aryl, cyclohexyl, 4-cyclohexylcyclohexyl, perhydro-1- or 2-naphthyl or piperidyl radical, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkynyl, hydroxyalkyl, cycloalkyl, cycloalkenyl or arylalkyl, or R.sup.1 and R.sup.2 together form an alkylene group and, together with the N atom, form a ring, and acid addition salts thereof, with the exception of compounds in which X is a single bond, Y is cyclohexyl, R.sup.1 and R.sup.2 are hydrogen or methyl, and the compounds in which X is C.sub.6 -, C.sub.7 - and C.sub.8 -alkyl, Y is hydrogen and R.sup.1 and R.sup.2 together with the N atom whose substituents they are form a 2,6-dimethylmorpholine radical, and fungicides containing such cyclohexylamines.
    Type: Grant
    Filed: September 20, 1989
    Date of Patent: November 6, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Zipperer, Ernst Buschmannm, Norbert Goetz, Ulrich Schirmer, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4954518
    Abstract: This invention relates to a 4H-1-benzopyran-4-one derivative represented by the formula: ##STR1## or a salt thereof, a process for producing the same and a pharmaceutical composition comprising the same as active ingredient.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: September 4, 1990
    Assignee: Toyama Chemical Company, Ltd.
    Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
  • Patent number: 4954498
    Abstract: The present invention provides tricyclic benzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl radical of the general formula: ##STR2## wherein R.sub.2, R.sub.3 and R.sub.4 can be the same or diferent as in claim 1. For A, B, C and D are understood those compounds where one or two of A, B, C or D are nitrogen. These compounds are useful to inhibit the aggregation of thrombocytes and erythrocytes, lower blood pressure and can increase the power of the heart.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: September 4, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Erwin Boehm, Klaus Strein
  • Patent number: 4925845
    Abstract: Gem 3 dialkyl or spiro 4 aryl or heteroaryl 5 heterocyclic 3 H indoles and their pharmaceutically acceptable salts are prepared. They are useful for reducing blood pressure producing a positive inotropic action influencing thrombocyte aggregation and improving microcirculation. Hydrazinophenyl heterocyclic intermeidates are also disclosed.
    Type: Grant
    Filed: February 24, 1988
    Date of Patent: May 15, 1990
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Lothar Kling, Bernd Muller-Beckmann
  • Patent number: 4914098
    Abstract: Substituted N-phenylthioureas, N-phenylisothioureas and N-phenylcarbodiimides of formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.8 cycloalkyl, polycyclic alkyl containing a total of 7 to 10 carbon atoms, C.sub.1 -C.sub.12 alkyl which is substituted by 1 to 12 halogen atoms, C.sub.1 -C.sub.4 alkyl which is substituted by one or two C.sub.3 -C.sub.6 cycloalkyl radicals, alkoxyalkyl containing a total of 3 to 10 carbon atoms, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical, C.sub.1 -C.sub.5 alkyl which is substituted by a phenyl radical which is in turn substituted by one or two members selected from the group consisting of halogen, methyl, methoxy and ethoxy; or is C.sub.3 -C.sub.10 -alkenyl or C.sub.3 -C.sub.10 alkynyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.3 is C.sub.1 -C.sub.4 alkyl, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, and R.sub.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: April 3, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund, Odd Kristiansen
  • Patent number: 4894181
    Abstract: Carbocyclic compounds of the formula I ##STR1## wherein Q is a benzene or cyclohexane ring or a naphthalene system, X is in each case --CH.sub.2 --(CH.sub.2).sub.p -- where it is also possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O--, --S--, --CO--, --O--CO--, --CO--O-- or --CH.dbd.CH--,p is 0, 1 or 2,A.sup.1 and A.sup.2 independently of one another are each a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by halogen atoms and/or CH.sub.3 groups and/or CN groups and in which it would also be possible for one or more CH groups to be replaced by N atoms, a 1,4-cyclohexylene group wherein it would also be possible for one or two non-adjacent CH.sub.2 groups to be replaced by --O-- and/or --S--, a piperidine-1,4-diyl group or a 1,4-bicyclo[2.2.2]octylene group,Z is --CO--O--, --O--CO--, --O--, --CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CHCN--CH.sub.2 --, --CH.sub.2 --CHCN--, --CH.dbd.CH--, --CH.dbd.N--, --N.dbd.CH--, --NO.
    Type: Grant
    Filed: May 16, 1988
    Date of Patent: January 16, 1990
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Klaus Praefcke, Bernd Kohne, Eike Poetsch
  • Patent number: 4882342
    Abstract: The present invention concerns new 5-alkylbenzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl ring of the formula: ##STR2## or R.sub.1 is naphthyl, heterocycle or a bicyclic heterocycle and R.sub.1 -R.sub.7 are described in claim 1.These compounds are useful for prophylaxis or treatment of heart and circulatory disease especially to increase contractility of the heart, lower blood pressure and/or influence the thrombocyte function and improve the microcirculation.
    Type: Grant
    Filed: October 6, 1987
    Date of Patent: November 21, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Wolfgang von der Saal, Jens-Peter Holck, Alfred Mertens, Bernd Muller-Beckmann, Lothar Kling
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4853151
    Abstract: Dispirotetradecanes of the formula I ##STR1## wherein R.sup.1 and R.sup.2 are each independently of each other alkyl containing 1 to 12 carbon atoms wherein one or more non-adjacent CH.sub.2 groups may also be replaced by --O--, --CO--, --CO--O--, --O--CO--, --O--COO-- and/or --CH.dbd.CH-- (trans), one of the radicals R.sup.1 and R.sup.2 also being H, F, Cl, Br, I, CN, NO.sub.2, NCS,A.sup.1 and A.sup.2 are each independently of each other trans-1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, or 1,4-phenylene wherein one or more CH groups may also be replaced by N, with it also being possible optionally for A.sup.1 and A.sup.2 to be substituted laterally or axially by F, Cl, CN, CH.sub.3,Z.sup.1 and Z.sup.2 are each independently of each other --C--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 O--, --OCH.sub.2 -- or a single bond,m and n are each 0, 1 or 2,(m+n) 0, 1 or 2,X.sup.1, X.sup.2, X.sup.3 and X.sup.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: August 1, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankfter Haftung
    Inventors: Fritz Vogtle, Wolfgang Calaminus
  • Patent number: 4853381
    Abstract: The invention provides compounds of the general formula (I) ##STR1## whereinAr represents a phenyl group optionally substituted by one or more substituents selected from halogen atoms, or the groups C.sub.1-6 alkyl, C.sub.1-6 alkoxy, nitro, --(CH.sub.2).sub.q R [where R is hydroxy, --NR.sup.3 R.sup.4 (where R.sup.3 and R.sup.4 each represent a hydrogen atom or a C.sub.1-4 alkyl group, or --NR.sup.3 R.sup.4 forms a saturated heterocyclic amino group which has 5-7 ring members and optionally contains in the ring one or more atoms selected from --O--, or --S-- or a group --NH-- or --N(CH.sub.3)--), --NR.sup.5 COR.sup.6 (where R.sup.5 represents a hydrogen atom or a C.sub.1-4 alkyl group, and R.sup.6 represents a hydrogen atom or a C.sub.1-4 alkyl, C.sub.1-4 alkoxy, phenyl or --NR.sup.3 R.sup.4 group), --NR.sup.5 SO.sub.2 R.sup.7 (where R.sup.7 represents a C.sub.1-4 alkyl, phenyl or --NR.sup.3 R.sup.4 group), --COR.sup.8 (where R.sup.8 represents hydroxy, C.sub.1-4 alkoxy or --NR.sup.3 R.sup.4), --SR.sup.
    Type: Grant
    Filed: October 15, 1986
    Date of Patent: August 1, 1989
    Assignee: Glaxo Group Limited
    Inventors: Harry Finch, Lawrence H. C. Lunts, Alan Naylor, Ian F. Skidmore, Ian B. Campbell
  • Patent number: 4851406
    Abstract: The present invention provides indole derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, carboxyl, cyano, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or aryl radical, R.sub.2 is a hydrogen atom or an alkyl, trihalogenomethyl, hydroxyl, cycloalkyl, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl radical; R.sub.2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 5 heteroatoms, the heteroatoms of the five- and six-membered rings being the same or different and being nitrogen, oxygen or sulphur and one or more of the nitrogen atoms optionally carrying an oxygen atom, the said five- and six-membered rings optionally being substituted by one or more alkyl, alkoxy, alkylthio, oxo, hydroxyl, nitro, amino, halogen or cyano groups; or R.sub.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: July 25, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
  • Patent number: 4843069
    Abstract: A compound of the general formula I(BH.sub.n).sub.m [RuX.sub.3+nm-q-r.sup.(OH).sub.r (BH.sub.p).sub.3-nm+q ].sub.1+p+q IwhereinB denotes a mononuclear or polynuclear basic heterocyclic radical containing one or more nitrogen atoms,X denotes chlorine or bromine,m denotes 1 or 2,n denotes 1 or 2, the sum of n and m being not greater than 3,p denotes 0 or 1, but not 1 if n is 1,q denotes 0 or 1, but not 1 if p is 1 andr denotes 0 or 1,show an antitumoral activity and are therefore suitable as a chemotherapeutic for the treatment of cancers.
    Type: Grant
    Filed: April 25, 1986
    Date of Patent: June 27, 1989
    Assignee: Asta Pharma AG
    Inventors: Heimo Keller, Bernhard Keppler
  • Patent number: 4835280
    Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: May 30, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
  • 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: 4820839
    Abstract: Nitrogen-containing heterocyclic esters of the formula I,R.sup.1 -A.sup.1 -Z.sup.1 -A.sup.2 -[Z.sup.2 -A.sup.3 ].sub.m -R.sup.2 Iin which R.sup.1, R.sup.2, A.sup.1, A.sup.2, A.sup.3, Z.sup.1, Z.sup.2 and m have the meaning specified in patent claim 1, are suitable as components of smectic liquid-crystalline phases.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Joachim Krause, Andreas Wachtler, Volker Reiffenrath, Bernhard Scheuble, Reinhard Hittich
  • Patent number: 4741765
    Abstract: Benzenesulfonamide compounds such as N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl-4 -oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide and N-[(4-methoxy-6-methyl-pyrimidin-2-yl)aminocarbonyl]-1,4-dihydro-3-methyl- 4-oxo-1-phenyl-indeno[1,2-C]pyrazole-5-sulfonamide, agricultural compositions containing them, and their herbicidal utility are disclosed.
    Type: Grant
    Filed: April 3, 1987
    Date of Patent: May 3, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Robert J. Pasteris, Ramaurthi Muthukrishnan
  • Patent number: 4689414
    Abstract: Cardiovascular activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof, wherein R.sub.1 is alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.2, --(CH.sub.2).sub.p --Y.sub.3 or halo substituted alkyl;R.sub.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, --(CH.sub.2).sub.n --Y.sub.1, or halo substituted alkyl;R.sub.3 is hydrogen, alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.2, --(CH.sub.2).sub.p --Y.sub.3, or halo substituted alkyl;R.sub.4 is aryl or heterocyclo;R.sub.5 is hydrogen, alkyl, aryl, arylalkyl, cyano, nitro, ##STR2## Y.sub.1 is cycloalkyl, aryl, heterocyclo, hydroxyl, alkoxy, aryl-(CH.sub.2).sub.m --O--, mercapto, alkylthio, aryl-(CH.sub.2).sub.m --S--, amino, substituted amino, carbamoyl, ##STR3## Y.sub.2 is cycloalkyl, aryl, heterocyclo, carbamoyl, ##STR4## amino, or substituted amino; m is 0 or an integer of 1 to 6;n is an integer of 1 to 6; andp is an integer of 2 to 6.
    Type: Grant
    Filed: February 24, 1986
    Date of Patent: August 25, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 4686227
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is lower alkyl,R.sup.3 is hydrogen, halogen or ar(lower)alkoxy, andR is lower alkanoyl, nitroso, amino, carboxy, esterified carboxy, carbamoyl, hydroxycarbamoyl, haloformyl, aminomethyleneamino which may be substituted with cyano or lower alkyl, iminomethylamino which may be substituted with cyano or lower alkyl, or a group of the formula: --A--R.sup.2 in whichA is lower alkylene andR.sup.2 is di(lower)alkylamino, cyano, lower alkoxy, N-containing heterocyclic group which may have suitable substituent(s), lower alkynyloxy, lower alkenyloxy, lower alkylthio, amino(lower)alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, carboxy, esterified carboxy, carbamoyl, hydroxycarbamoyl, hydroxy, lower alkanoyloxy, heterocyclicamino (lower)alkylthio having two oxo groups, hydrogen or a group of the formula: ##STR2## in which R.sup.4, R.sup.5 and R.sup.6 are each lower alkyl andX is an acid residue,and pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: June 17, 1985
    Date of Patent: August 11, 1987
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Ikuo Ueda, Youichi Shiokawa, Masayuki Kato, Nobukiyo Konishi, Atsushi Akahane
  • Patent number: 4684656
    Abstract: Cardiovascular activity is exhibited by compounds having the formula ##STR1## and pharmaceutically acceptable salts thereof wherein X is oxygen or sulfur;R.sub.1 is alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.1, or halo substituted alkyl;R.sub.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, --(CH.sub.2).sub.n --Y.sub.1, or halo substituted alkyl;R.sub.3 is hydrogen, alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.2, --(CH.sub.2).sub.p --Y.sub.3, or halo substituted alkyl;R.sub.4 is aryl or heterocyclo;Y.sub.1 is cycloalkyl, aryl, heterocyclo, hydroxyl, alkoxy, aryl--(CH.sub.2).sub.m --O--, mercapto, alkylthio, aryl--(CH.sub.2).sub.m --S--, amino, substituted amino, carbamoyl, ##STR2## Y.sub.2 is cycloalkyl, aryl, heterocyclo, carbamoyl, ##STR3## Y.sub.3 is hydroxyl, alkoxy, aryl--(CH.sub.2).sub.m --O--, mercapto, alkylthio, aryl--(CH.sub.2).sub.
    Type: Grant
    Filed: March 14, 1986
    Date of Patent: August 4, 1987
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Karnail Atwal
  • Patent number: 4680338
    Abstract: A selective bifunctional sequential linker has the formulaY.dbd.C.dbd.N--Q--A--C(O)--Zwherein Q is a homoaromatic or heteroaromatic ring system; A is a single bond or an unsubstituted or substituted divalent C.sub.1-30 bridging group; Y is O or S; and Z is Cl, Br, I, N.sub.3, N-succinimidyloxy, imidazolyl, 1-benzotriazolyloxy, OAr where Ar is an electron-deficient activating aryl group, or OC(O)R where R is --A--Q--N.dbd.C.dbd.Y or C.sub.4-20 tertiary-alkyl. A method for activating an amine function towards reaction with a second amine involves reacting the amine with the foregoing linker. The resultant isocyanate or isothiocyanate derivative can then be reacted with a second amine to form a urea or thiourea conjugate.The linker is useful for producing conjugates of ligands with amine-containing polymers and/or proteins, especially for forming antibody conjugates with chelators, drugs, enzymes, detectable labels and the like.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: July 14, 1987
    Assignee: Immunomedics, Inc.
    Inventor: Boby M. Sundoro
  • Patent number: 4658027
    Abstract: A process for the preparation of a 1-(2-oxyaminosulphonyl-phenylsulphonyl)-urea of the formula ##STR1## in which R.sup.1 is an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aralkyl and aryl,R.sup.2 is hydrogen or an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl and aralkyl, andR.sup.3 is an optionally substituted and/or optionally fused six-membered aromatic heterocyclic radical containing at least one nitrogen atom,comprising reacting water with a benzodisultam of the formula ##STR2## at a temperature between 0.degree. C. and 100.degree. C. The products are herbicidally active.
    Type: Grant
    Filed: August 23, 1985
    Date of Patent: April 14, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Diehr, Christa Fest, Rolf Kirsten, Joachim Kluth, Klaus-Helmut Muller, Theodor Pfister, Uwe Priesnitz, Hans-Jochem Riebel, Wolfgang Roy
  • Patent number: 4656171
    Abstract: Compounds of the formula ##STR1## wherein A, B, C and D are each independently --N.dbd. or --CH.dbd., provided, however, that at least two of them must be --N.dbd., and when A and C are both --N.dbd., at least one or both of B and D must be --N.dbd.; andR.sub.1, R.sub.2 and R.sub.3 are substituents of diverse types;tautomers thereof; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds are useful as cardiotonics.
    Type: Grant
    Filed: November 27, 1984
    Date of Patent: April 7, 1987
    Assignee: Dr. Karl Thomae GmbH
    Inventors: Volkhard Austel, Norbert Hauel, Joachim Heider, Manfred Reiffen, Jacobus C. A. Van Meel, Willi Diederen
  • Patent number: 4601846
    Abstract: The invention relates to liquid crystal compounds for the guest-host effect having a positive contrast, pure red color and exhibiting excellent stability. The compounds herein are derivatives of tetrazine of the general formula: ##STR1## in which m and n are 1 to 10. Other related compounds, mixtures and compositions thereof, and opto-electronic displays are described also.
    Type: Grant
    Filed: April 13, 1984
    Date of Patent: July 22, 1986
    Assignee: VEB Werk fuer Fernsehelektronik im VED Kombinat Mikroelektronik
    Inventors: Dietrich Demus, Horst Zaschke, Gerhard Pelzl, Hartmut Enzenberg, Andreas Isenberg
  • Patent number: 4549018
    Abstract: A process for addition curing organosilicone compositions using as catalysts rodium- or iridium-nitrogen complex compounds having the formulae:(a) monometallic complexes, (L)MX(Y).sub.2, and(b) bimetallic complexes, (L) [RhX(CO).sub.2 ].sub.2, whereinM is a rhodium or iridium metal atom,L is a single or fused heterocyclic ligand comprising at least one five- or six-membered ring, said ligand having 2 to 4 ring nitrogen atoms in the same ring,Y is an uncharged ligand that fills one or two coordination positions of the metal atom, andX is Cl, Br, I, or CN.Preparation of the novel catalysts is disclosed. The cured compositions are useful as molded articles, such as gaskets, O-rings, and tubing.
    Type: Grant
    Filed: August 11, 1983
    Date of Patent: October 22, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Allen R. Siedle
  • Patent number: 4517182
    Abstract: The title compounds are provided as well as a method for their production, pharmaceutical compositions comprising the compounds, and a method of treatment using the compounds in dosage form. Compounds of the invention have pharmacological properties and are useful antimicrobial agents and antileukemic agents.
    Type: Grant
    Filed: April 3, 1984
    Date of Patent: May 14, 1985
    Assignee: Warner-Lambert Company
    Inventor: Chia-Chung Cheng
  • Patent number: 4511715
    Abstract: A hydrosilation process is disclosed for the reaction between silicon-hydrogen bonds and compounds having aliphatic carbon atoms linked by multiple bonds using as catalysts novel platinum-nitrogen complex compounds of the following classes:(a) monometallic complexes, (L)PtX.sub.2 (Y),(b) bimetallic complexes, (L)(PtX.sub.2).sub.2 (Y).sub.2,(c) ionic complexes, (L)PtX.sub.2 (Y)(Z), and(d) reduced forms of said monometallic complexes having the formulae:(1) H[(PNZ)PtX.sub.2 (Q)].sub.2,(2) [(PNZ)PtX.sub.2 (Q)].sub.2.sup.- A.sup.+, and(3) [H(PNZ)PtCl.sub.2 (C.sub.2 H.sub.4)].sub.3 PtCl.sub.
    Type: Grant
    Filed: July 27, 1982
    Date of Patent: April 16, 1985
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Frederick J. Palensky, Allen R. Siedle
  • Patent number: 4504475
    Abstract: The title compounds are provided as well as a method for their production, pharmaceutical compositions comprising the compounds, and a method of treatment using the compounds in dosage form. Compounds of the invention have pharmacological properties and are useful antileukemic agents.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: March 12, 1985
    Assignee: Warner Lambert Company
    Inventor: Chia C. Cheng
  • Patent number: 4459407
    Abstract: A 1-(4-aminobenzyl)-2,3-dioxopiperazine derivative represented by the formula: ##STR1## and a salt thereof have excellent carcinostatic activity but a low toxicity. Therefore, said compounds are useful as medicines and also as intermediates.
    Type: Grant
    Filed: February 2, 1982
    Date of Patent: July 10, 1984
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Takako Hori, Chosaku Yoshida, Yasuo Kiba, Ryuko Takeno, Joji Nakano, Jun Nitta, Sumiko Kishimoto, Shohachi Murakami, Hisatsugu Tsuda, Isamu Saikawa
  • Patent number: 4414221
    Abstract: The compounds of the formula: ##STR1## wherein R.sup.1 represents phenyl substituted in at least the 2-position by fluorine, chlorine, bromine or iodine, R.sup.2 represents a group R.sup.3, --OR.sup.3, --SR.sup.3 or --NR.sup.3 R.sup.4 where R.sup.3 represents hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, alkenyl of 2 to 6 carbon atoms, cycloalkenyl of 3 to 7 carbon atoms, alkynyl of 2 to 6 carbon atoms, phenyl, phenylalkyl of 7 to 10 carbon atoms or naphthyl, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy or alkylthio groups of 1 to 6 carbon atoms, nitro groups, cyano groups or mercapto groups, R.sup.4 represents a group as defined for R.sup.
    Type: Grant
    Filed: March 20, 1981
    Date of Patent: November 8, 1983
    Assignee: FBC Limited
    Inventors: John H. Parsons, Peter J. West
  • Patent number: 4358589
    Abstract: A nematic liquid crystal compound adapted for the modulation of the transmitted or incident light and reproduction in color of numerals, symbols and images by electro-optical devices, the said compound having the formula ##STR1## wherein R.sup.1 .dbd.Br--, Cl--, C.sub.n H.sub.2n+1 --, C.sub.n H.sub.2n+1 O--, n being 1 to 10,R.sup.2 .dbd.C.sub.n H.sub.2n+1 --, n being 2 to 10,R.sup.3 .dbd.C.sub.n H.sub.2n+1 --, C.sub.n H.sub.2n+1 O--, n being 1 to 10,R.sup.4 .dbd.C.sub.n H.sub.2n+1 --, C.sub.n H.sub.2n+1 O--, n being 1 to 10.
    Type: Grant
    Filed: May 7, 1980
    Date of Patent: November 9, 1982
    Assignee: Veb Werk fur Fernsehelektronik im Veb Kombinat Mikroelektronik
    Inventors: Herrmann Schubert, Dietrich Demus, Horst Zaschke, Frank Kuschel, Gerhard Pelzl, Hans-Ulrich Nothnikz, Willibald Schliemann
  • Patent number: 4356103
    Abstract: Liquid crystal compound for color modulation of light in electro-optical devices characterized by an oriented smectic C-phase with positive dielectric anisotropy. The compound has the property of a dichroitic dyestuff.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: October 26, 1982
    Assignee: Veb Werk fur Fernsehelektronik
    Inventors: Herrmann Schubert, Gerhard Pelzl, Horst Zaschke, Dietrich Demus, Hans-Ulrich Nothni, Frank Kuschel
  • Patent number: 4348298
    Abstract: A nematic liquid crystal mixture for modulation of the transmitted or incident light and for rendition of colored numerals, symbols and images in electro-optical devices, the said mixture comprising(a) a nematic liquid crystal adapted for reorientation in an electrical field due to its dielectric anisotropy and(b) a dichroic dyestuff adapted for simultaneous orientation changes together with the said nematic liquid crystal between a light absorption and a light transmission position based on the guest-host effect, the said dyestuff being an s-tetrazine derivative having an elongate molecular structure and having the formula ##STR1## wherein X is ##STR2## R.sup.1 and Y is R.sup.2 -- or ##STR3## R.sup.1 being H--, F--, Cl--, Br--, J--, O.sub.2 N--, NC--, HO--, H.sub.2 N--, C.sub.n H.sub.2n+1 NH--, C.sub.n H.sub.2n+1 (CH.sub.3)N--, C.sub.n H.sub.2n+1" --, C.sub.n H.sub.2n+1 O--, C.sub.n H.sub.2n+1 S--, C.sub.n H.sub.2n+1 COS--, C.sub.n H.sub.2n+1 COO--, C.sub.n H.sub.2n+1 OOC--, C.sub.n H.sub.2n+1 CO-- or C.sub.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: September 7, 1982
    Assignee: VEB Werk fur Fernsehelektronik im Veb Kombinat Mikroelektronik
    Inventors: Horst Zaschke, Rudolf Wolff, Gerhard Pelzl, Dietrich Demus
  • Patent number: 4339513
    Abstract: A process and recording medium for four-level, two-photon holography are provided. These media are particularly useful for recording holograms using continuous wave lasers. The recording medium is formed by a transport resin containing a tetrazine compound.
    Type: Grant
    Filed: November 20, 1980
    Date of Patent: July 13, 1982
    Assignee: International Business Machines Corporation
    Inventors: David C. Alvarez, Gary C. Bjorklund, Donald M. Burland
  • Patent number: 4237127
    Abstract: The substituted tetrazines of the formula: ##STR1## and of the formula: ##STR2## wherein: R.sup.1, R.sup.2 and R.sup.4 each represent hydrogen, phenyl, alkyl of 1 to 6 carbon atoms, or alkenyl or alkynyl of 3 to 6 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, hydroxy groups, cyano groups, carboxy groups, alkoxycarbonyl groups of 2 to 5 carbon atoms, or alkoxy groups of 1 to 4 carbon atoms; or R.sup.1 and R.sup.2 together represent a single bond; R.sup.3 represents alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or phenylalkyl of 7 to 10 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy groups of 1 to 6 carbon atoms, nitro groups, cyano groups, mercapto groups, or alkylmercapto groups of 1 to 4 carbon atoms; and R.sup.6 represents a phenyl group substituted in at least the 2-position by fluorine, chlorine, bromine or iodine; are effective to combat acarids and their eggs.
    Type: Grant
    Filed: May 21, 1979
    Date of Patent: December 2, 1980
    Assignee: Fisons Limited
    Inventor: John H. Parsons