1,3,4-thiadiazoles (including Hydrogenated) Patents (Class 548/136)
  • Patent number: 5409944
    Abstract: Disclosed are compounds of Formula I useful in the treatment of cyclooxygenase mediated diseases such as pain, fever and inflammation of a variety of conditions including rheumatic fever, symptoms associated with influenza or other viral infections, common cold, low back and neck pain, dysmenorrhea, headache, toothache, sprains and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis degenerative joint diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns, injuries.
    Type: Grant
    Filed: March 12, 1993
    Date of Patent: April 25, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
  • Patent number: 5405969
    Abstract: The invention provides a process for making a thioether compound having the formula:A--S--Rcomprising reacting:(1) Compound I having the formula:A--H (I)where A comprises a carbon atom bonded to H where that carbon is either capable of ionizing to a nucleophilic state or is conjugated to such an atom, with(2) Compound II having the formula:H--SR or RSSR (II)wherein R is selected from the group consisting of:(a) a substituted or-unsubstituted aryl group or alicyclic group, said groups being carbocyclic or heterocyclic, and(b) a thiocarbonyl group,in the presence of a base and an oxidizing agent that is free of reactive halogen and that is capable of oxidizing H--SR to RSSR.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: April 11, 1995
    Assignee: Eastman Kodak Company
    Inventors: Charles W. Wright, Joan C. Potenza, John E. Leary, Jr., Chang K. Kim
  • Patent number: 5393459
    Abstract: The invention relates to optically active compounds of the formula I ##STR1## in which R is an alkyl or alkenyl radical having up to 15 carbon atoms which is unsubstituted, monosubstituted by --CN or at least monosubstituted by fluorine or chlorine, it also being possible for a CH.sub.2 group in these radicals to be replaced by --O--, --CO--, --O--CO--, --CO--O-- or --O--CO--O--,A.sup.1 and A.sup.2 are each, independently of one another, a 1,4-phenylene radical, pyridine-2,5-diyl radical, pyrimidine-2,5-diyl radical, pyrazine-2,5-diyl radical, pyridazine-3,6-diyl radical, 1,3,4-thiadiazole-2,5-diyl radical, 1,2,4-thiadiazole-3,5-diyl radical or trans-1,4-cyclohexylene radical, each of which is unsubstituted or substituted by one or two fluorine atoms, and in which, in addition, one or two non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--, and/or a CH group,Z.sup.1, Z.sup.2 and Z.sup.3 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.
    Type: Grant
    Filed: October 5, 1992
    Date of Patent: February 28, 1995
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Andreas Wachtler, Thomas Geelhaar, Reinhard Hittich, Ekkehard Bartmann, Joachim Krause, Eike Poetsch
  • Patent number: 5387689
    Abstract: The invention relates to chiral valerolactone derivatives of the formula I ##STR1## wherein R.sup.1 is C.sub.1-18 alkyl in which one or two non-adjacent --CH.sub.2 groups are optionally replaced by --O--, --CO--O--, --O--CO-- or --S--,A is --H.sub.2 --, --C--(CH.sub.3).sub.2 -- or --CH.sub.2 CH.sub.2,Sp is a spacer, which optionally contains a chiral carbon atom,Z.sup.0 is --COO--, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, --C.tbd.C-- or --CH.tbd.CH--,MG is a mesogenic group, andn and p are each 0 or 1,and the use thereof as components of liquid-crystalline media for electrooptical displays.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: February 7, 1995
    Assignee: Merck Patent Gesellschaft Mit Beschrankter Haftung
    Inventors: Volker Reiffenrath, Ulrich Finkenzeller
  • Patent number: 5380460
    Abstract: Chiral, nonracemic compounds of the general formula: ##STR1## wherein m and n are either both zero, both equal one or n is equal to one and m is equal to zero, X and Y and Z are halogens, R' is an alkyl, alkoxyl, alkenyl, thioalkyl, thioether, ether, or alkylsilyl group containing three to fifteen carbon atoms, and R is an alkyl group having one to fifteen carbon atoms and where Ar is:--A.sub.a --(E).sub.e --B.sub.b --(F).sub.f --D.sub.d --where A, B and D independently of one another are aromatic rings which are selected from the group consisting of a phenyl, a pyridine ring, a pyrimidine ring, a pyridizine ring, a pyrazine ring and a thiadiazole ring, wherein a, b and d are integers from 0-3 such that a+b+d=2-3, where E and F independently of one another are linking groups selected from the group consisting of a --CH.sub.2 --CH.sub.2 --, --CH.sub.2 --O--, --CH.sub.2 --S--, --O--CH.sub.2 --, --S--CH.sub.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: January 10, 1995
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, William N. Thurmes, David M. Walba
  • Patent number: 5378680
    Abstract: Dicarboximides of the formulae Ia, Ib and Ic ##STR1## where X is oxygen or sulfur,R.sup.1 is hydrogen, halogen, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, haloalkoxy, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, phenyl, phenylalkyl, phenoxy or phenylthio, a 5-membered or 6-membered saturated or aromatic heterocyclic radical containing one or two hetero atoms selected from the group consisting of oxygen, sulfur and nitrogen, where the stated organic radicals may be further substituted, andR.sup.2 is hydrogen, hydroxyl, alkoxy, alkyl, cycloalkyl, alkenyl, alkynyl, di-C.sub.1 -C.sub.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: January 3, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Maywald, Klaus Ditrich, Thomas Kuekenhoehner, Gerhard Hamprecht, Wolfgang Freund, Karl-Otto Westphalen, Matthias Gerber, Helmut Walter
  • Patent number: 5374642
    Abstract: Hydroquinone diethers of the general formula I ##STR1## where R.sup.1 is hydrogen, halogen or C.sub.1 -C.sub.6 -alkyl, A and B are each unsubstituted or substituted methylene, ethylene or propylene and X and Y are each unsubstituted or substituted hetaryl, processes for their preparation and pesticides.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: December 20, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Kardorff, Christoph Nuebling, Hans Theobald, Thomas Kuekenhoehner, Hans-Juergen Neubauer, Joachim Leyendecker, Christoph Kuenast, Peter Hofmeister, Wolfgang Krieg
  • Patent number: 5374726
    Abstract: A process is provided for the preparation of 10-deazaaminopterins and 5,10- and 8,10-dideazaaminopterins starting from the corresponding homoterephthalic acid diester coupling the corresponding dicarboxylic acid diester having the formula: ##STR1## with the corresponding diaminopterin 6-methylene halide having the formula: ##STR2## thereby forming a pteroic acid diester having the formula: ##STR3## hydrolysing the two ester groups to form the corresponding carboxylic acid groups, and then monodecarboxylating the diacid, thereby removing the carboxylic acid group attached to the carbon alpha to the A group and forming a pteroic acid.
    Type: Grant
    Filed: March 9, 1993
    Date of Patent: December 20, 1994
    Inventors: Joseph I. DeGraw, William T. Colwell, James R. Piper
  • Patent number: 5366657
    Abstract: Geminal dimethylalkyl compounds, process for their preparation and their use in liquid-crystalline mixtures Geminal dimethylalkyl compounds of the formula (I) ##STR1## in which: R.sup.1 is, for example, straight-chain or branched (with or without an asymmetric carbon atom) alkyl or alkenyl having 2 to 16 carbon atoms,A.sup.1, A.sup.2 and A.sup.3 are, for example, identical or different 1,4-phenylene, 1,4-cyclohexylene or pyrimidine-2,5-diyl,M.sup.1 and M.sup.2 are, for example, identical or different CO--O or O--CO,G is for example, identical or different straight-chain or branched alkylene having 1 to 16 carbon atoms,k, l, m and n are zero or 1, andR.sup.6 is straight-cain alkyl having 1 to 10 carbon atoms,can advantageously be employed in liquid-crystalline mixtures. In liquid-crystalline mixtures, said compounds result in a melting point depression, in a shift in the temperature limit of the S.sub.c phase in ferroelectric mixtures and in other improvements of important electrooptical characteristic values.
    Type: Grant
    Filed: July 24, 1992
    Date of Patent: November 22, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gerhard Illian, Ingrid Muller, Takamasa Harada
  • Patent number: 5366984
    Abstract: Methyl .alpha.-arylacrylates substituted by a heterocyclic radical and having the general formula ##STR1## where R is alkyl, alkenyl, haloalkyl, cycloalkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen or aryl, the aromatic ring being unsubstituted or substituted, Het is a five-membered heteroaromatic ring which is unsubstituted or substituted and has from one to three heteroatoms, and A is ethenylene, ethylene, methyleneoxy or methylenethio, and fungicides and pesticides containing these compounds.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: November 22, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
  • Patent number: 5364856
    Abstract: 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[cd]indoles are provided which are useful in modifying the function of serotonin in mammals.
    Type: Grant
    Filed: September 30, 1992
    Date of Patent: November 15, 1994
    Assignee: Eli Lilly and Company
    Inventors: Richard N. Booher, David E. Lawhorn, Charles J. Paget, Jr., John M. Schaus
  • Patent number: 5342937
    Abstract: A solvent soluble heterocyclic o-hydroxy thione carrying a lipophilic group and the process for the selective extraction of gallium, and certain other related metals, especially from solutions containing excess aluminium.
    Type: Grant
    Filed: October 7, 1991
    Date of Patent: August 30, 1994
    Assignees: Zeneca, Limited, Nerco, Inc.
    Inventors: Peter W. Austin, Peter M. Quan, Peter A. Tasker, Derek Thorp
  • Patent number: 5342849
    Abstract: Phenoxyalkyl-substituted heteroaromatics of the formulae Ia and Ib ##STR1## where the substituents have the following meanings: R.sup.1 C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -alkynyl, C.sub.1 -C.sub.12 -haloalkyl,C.sub.2 -C.sub.12 -haloalkenyl, C.sub.2 -C.sub.12 -haloalkynyl, C.sub.3 -C.sub.12 -alkoxyalkyl,C.sub.3 -C.sub.8 -cycloalkyl, C.sub.4 -C.sub.12 -cycloalkylalkyl, C.sub.3 -C.sub.8 -halocycloalkyl,C.sub.4 -C.sub.12 -halocycloalkylalkyl, C.sub.4 -C.sub.12 -cycloalkylhaloalkyl orC.sub.4 -C.sub.12 -halocycloalkylhaloalkyl;Z hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano in the case of Ia and hydrogen, halogen, or C.sub.1 -C.sub.4 -alkyl in the case of Ib;X O, S, SO.sub.2 ;Q.sub.a substituted or unsubstituted azole;Q.sub.b substituted or unsubstituted heteroaromatic;methods of manufacturing compounds Ia and Ib, and their use for combating pests.
    Type: Grant
    Filed: September 9, 1992
    Date of Patent: August 30, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Leyendecker, Hans-Juergen Neubauer, Uwe Kardorff, Christoph Kuenast, Wolfgang Krieg, Peter Hofmeister
  • Patent number: 5340810
    Abstract: The invention provides compounds of formula (I): ##STR1## or a physiologically acceptable salt or solvate thereof wherein R.sup.1 represents a hydrogen atom or a halogen atom or a group selected from C.sub.1-6 alkyl and C.sub.1-6 alkoxy;R.sup.2 represents a phenyl group substituted by a group selected from ##STR2## and optionally further substituted by one or two substituents selected from halogen atoms, C.sub.1-6 alkoxy, hydroxy, and C.sub.1-6 alkyl;R.sup.3 represents the group ##STR3## R.sup.4 and R.sup.5, which may be the same or different each independently represent a hydrogen atom or a halogen atom or a group selected from hydroxy, C.sub.1-6 alkoxy and C.sub.1-6 alkyl;R.sup.6 represents a hydrogen atom or a group selected from --NR.sup.9 R.sup.10 and a C.sub.1-6 alkyl group optionally substituted by one or two substituents selected from C.sub.1-6 alkoxy, hydroxy, C.sub.1-6 acyloxy and --SO.sub.2 R.sup.11 ;R.sup.7, R.sup.8 and R.sup.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: August 23, 1994
    Assignee: Glaxo Group Limited
    Inventors: John W. Clitherow, Malcolm Carter
  • Patent number: 5336436
    Abstract: Optically active oxirane derivatives containing a mesogenic molecular unit are suitable as dopes in liquid-crystal mixtures. They give liquid-crystalline ferroelectric phases having short response times and electroclinic phases having large electroclinic coefficients. A further advantage is that they induce a helix of very small pitch, so that they are also suitable for helix compensation in LC mixtures.
    Type: Grant
    Filed: June 22, 1992
    Date of Patent: August 9, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Scherowsky, Kirsten Gruneberg
  • Patent number: 5336420
    Abstract: An aromatic functional fluid, specifically a monoalkylated tetradecyl diphenyl oxide synthetic lubricant, contains a polymer-supported reaction product of an organic quaternary ammonium salt, derived from a mercapto-heterocycle and a quaternary ammonium salt. To produce the polymer-supported organic quaternary ammonium salt, the salt is reacted with a dicarboxylic acid or anhydride, specifically 2-dodecen-1-ylsuccinic anhydride. An arylamine antioxidant, such as alkylated phenyl naphthylamine, can be added to the polymer supported organic quaternary ammonium salt-treated functional fluid to impart extra antioxidant and stability properties.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: August 9, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Andrew G. Horodysky, Shih-Ying Hsu, Andrew Jeng, Leslie R. Rudnick
  • Patent number: 5332757
    Abstract: The invention concerns oxime derivatives of the formula I ##STR1## wherein R.sup.4 includes hydrogen, carboxy, carbamoyl, amino, cyano, trifluoromethyl, (1-4C)alkylamino, di-(1-4C)alkylamino and (1-4C)alkyl;R.sup.5 includes hydrogen, (1-4C)alkyl, (3-4C)alkenyl, (3-4C)alkynyl, (2-5C)alkanoyl, halogeno-(2-4C)alkyl and hydroxy-(2-4C)alkyl;Ar.sup.1 is phenylene or a heteroaryl diradical;A.sup.1 is a direct link to X.sup.1, or A.sup.1 is (1-4C)alkylene;X.sup.1 is oxy, thio, sulphinyl or sulphonyl;Ar.sup.2 is phenylene or a heteroaryl diradical;R.sup.1 is (1-4C)alkyl, (3-4C)alkenyl or (3-4C)alkynyl; andR.sup.2 and R.sup.3 together form a group of the formula -A.sup.2 -X.sup.2 -A.sup.3 - which together with the carbon atom to which A.sup.2 and A.sup.3 are attached define a ring having 5 or 6 ring atoms, wherein each of A.sup.2 and A.sup.3 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: February 8, 1993
    Date of Patent: July 26, 1994
    Assignees: Zeneca Limited, Zeneca PHARMA S A
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5328916
    Abstract: New heterocyclic compounds of the formulaX--W--CR.sup.1 R.sup.2 --CO--Y--NR.sup.3 --CHR.sup.4 --CR.sup.5 --CH.sub.2 --(CR.sup.6 R.sup.7).sub.r --Z--Het Iin which R.sup.1 to R.sup.7, W, X, Y, Z, r and Het have the meanings defined herein, and the salts thereof, inhibit the activity of human plasma renin.
    Type: Grant
    Filed: May 2, 1991
    Date of Patent: July 12, 1994
    Assignee: Merck Patent Gesellschaft mit Beschrankter Haftung
    Inventors: Peter Raddatz, Claus J. Schmitges, Klaus-Otto Minck
  • Patent number: 5312831
    Abstract: The invention relates to novel ureas and urethanes of Formula I: ##STR1## which stimulate cytokine production and may be used to accelerate recovery from neutropenia accompanying radio- or chemotherapy, bone marrow transplantation, or infections. Compounds in the invention or pharmaceutical compositions employing these compounds may be useful in the treatment of cancer, AIDS, aplastic anemia, myelodysplastic syndrome, and infectious diseases, and in the enhancement of immune response.
    Type: Grant
    Filed: May 12, 1993
    Date of Patent: May 17, 1994
    Assignee: American Cyanamid Company
    Inventors: Semiramis Ayral-Kaloustian, Steven R. Schow, Mila T. Du, James J. Gibbons, Jr.
  • Patent number: 5300655
    Abstract: This invention relates to novel 3-substituted-2-oxindole derivatives which are inhibitors of prostaglandin H.sub.2 synthase, 5-lipoxygenase and interleukin-1 biosynthesis. The compounds of the invention are useful as inhibitors of prostaglandin H.sub.2 synthase and interleukin-1 biosynthesis, per se, and as analgesic, antiinflammatory and antiarthritic agents in the treatment of chronic inflammatory diseases. This invention also relates to pharmaceutical compositions comprising said 3-substituted-2-oxindole derivatives; to methods of inhibiting prostaglandin H.sub.2 synthase and biosynthesis of interleukin-1; and to treating chronic inflammatory diseases in a mammal with said compounds. Further, this invention relates to certain novel carboxylic acids useful as intermediates in the preparation of the 3-substituted-2-oxindole derivatives of this invention and to a process for the preparation of the 3-substituted-2-oxindole derivatives.
    Type: Grant
    Filed: December 16, 1992
    Date of Patent: April 5, 1994
    Assignee: Pfizer Inc.
    Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
  • Patent number: 5292762
    Abstract: Compounds of the formula ##STR1## wherein A is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic;Y and Z are independently selected from the group consisting of O, S, and N--R;R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted phenyl, and substituted or unsubstituted heterocyclic; andX is selected from the group consisting of I and Br.are disclosed to useful as antimicrobials.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: March 8, 1994
    Assignee: Rohm and Haas Company
    Inventor: Adam C. Hsu
  • Patent number: 5290756
    Abstract: Compounds of the formula: ##STR1## wherein X is hydrogen, halo, trihalomethyl, alkyl, nitroor cyano; X.sup.1 is hydrogen, halo, or trihalomethyl; R.sup.1 and R.sup.2 are hydrogen, alkyl phenyl or benzyl; n is 1 to 5, and Z is halo, cyano, nitro, trihalomethyl, methylthio, methylsulfinyl, methylsulfonyl, acetyl, phenyl, or heterocycle, and compositions containing these compounds exhibit herbicidal activity.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: March 1, 1994
    Assignee: Rohm and Haas Company
    Inventors: Colin Swithenbank, Ted Fujimoto
  • Patent number: 5280032
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: September 8, 1992
    Date of Patent: January 18, 1994
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5276037
    Abstract: The invention concerns an aryl derivative of the formula I, ##STR1## wherein Ar.sup.1 is optionally substituted phenyl, naphthyl or a heterocyclic moiety, and X.sup.1 is oxy, thio, sulphinyl, sulphonyl, difluoromethylene, imino, (1-4C)alkylimino or optionally substituted (1-4C)alkylene, or X.sup.1 is a group of the formula--X.sup.4 --CR.sub.2 -- or --CR.sub.2 --X.sup.4 --whereinX.sup.4 is oxy, thio, sulphinyl, sulphonyl or carbonyl and each R is hydrogen, methyl or ethyl;each of Ar.sup.2 and Ar.sup.3 is optionally substituted phenylene;X.sup.2 is oxy, thio, sulphinyl or sulphonyl;R.sup.1 is (1-4C)alkyl; andR.sup.2 and R.sup.3 together form a group of the formula --A.sup.1 --X.sup.3 --A.sup.2 -- which together with the carbon atom to which A.sup.1 and A.sup.2 are attached define a ring having 5 to 7 ring atoms, wherein each of A.sup.1 and A.sup.2 is (1-3C)alkylene and X.sup.
    Type: Grant
    Filed: April 14, 1993
    Date of Patent: January 4, 1994
    Assignees: Imperial Chemical Industries PLC, ICI Pharma
    Inventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
  • Patent number: 5271864
    Abstract: Ferroelectric liquid crystal compounds and compositions containing cyclohexenyl derivatives are provided. Specifically provided are compounds of formula: ##STR1## wherein R.sub.1 and R.sub.2 can be an alkyl, cycloalkyl, alkenyl, alkoxy, thioalkyl, alkylsilyl group having from one to about twenty carbon atoms. Y denotes --COO--, --OOC--, --CH.sub.2 O--, or --OCH.sub.2 --; and Ar.sub.1 and Ar.sub.2, independently of one another, can be selected from the group consisting of phenyl rings, halogenated phenyl rings and nitrogen-containing aromatic groups. In preferred embodiments the compounds of this invention contain at least one nitrogen-containing aromatic ring. Ar.sub.1 and Ar.sub.2 can be selected from 1,4-phenyl, mono- or dihalogenated 1,4-phenyl, 2,5-pyridinyl, 2,5-pyrimidyl, 2,5-pyrazinyl, 2,5-thiadiazole, 3,6-pyridazinyl and 1,4-cyclohexyl either or both be chiral racemic groups or chiral nonracemic groups.
    Type: Grant
    Filed: August 7, 1992
    Date of Patent: December 21, 1993
    Assignee: Displaytech, Inc.
    Inventors: Michael D. Wand, Rohini T. Vohra, Kundalika M. More, William N. Thurmes
  • Patent number: 5256632
    Abstract: Herbicidal sulphonylated carboxamides of the formulaR.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)in whichn represents the numbers 0 or 1,A represents oxygen, iminio (NH) or methylene (CH.sub.2),R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, andR.sup.2 represents aryl or heteroaryl which are in each case optionally substituted,or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.
    Type: Grant
    Filed: June 18, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5254595
    Abstract: Aryloxypropanolaminotetralins with beta-antagonist activity of the formula ##STR1## wherein R is hydrogen, hydroxy or methoxy and Ar is an optionally substituted aromatic or heteroaromatic group, in optically active or inactive form as well as their acid addition salts are described.A process for their preparation and pharmaceutical compositions containing the compounds of formula (i) or their pharmaceutically acceptable acid addition salts, are also described.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: October 19, 1993
    Assignee: Elf Sanofi
    Inventors: Umberto Guzzi, Marco Baroni, Sergio Boveri, Luciano Manara, Alberto Bianchetti
  • Patent number: 5248682
    Abstract: The present invention is novel compounds which are 2-substituted-4,6-di-tertiarybutyl-5-hydroxy-1,3-pyrimidines and pharmaceutically acceptable acid addition or base salts thereof, pharmaceutical compositions and methods of use therefor. The invention compounds are now found to have activity as inhibitors of 5-lipoxygenase and/or cyclooxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever and the like. Thus, the present invention is also a pharmaceutical composition or method of manufacturing a pharmaceutical composition for the use of treating the noted conditions.
    Type: Grant
    Filed: August 3, 1992
    Date of Patent: September 28, 1993
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Catherine R. Kostlan
  • Patent number: 5246952
    Abstract: Compounds of formula I ##STR1## wherein Z is thiazolyl or isothiazolyl, and X, R, R.sub.0, R.sub.1, R.sub.2 and R.sub.3 are as defined in the description, have valuable pharmaceutical properties and are effective especially against tumors.
    Type: Grant
    Filed: September 17, 1991
    Date of Patent: September 21, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Marc Lang
  • Patent number: 5245040
    Abstract: A process for the preparation of 1,3-disubstituted 2-nitroguanidines of the formula I ##STR1## in which R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl or a radical --CH.sub.2 B; A is an unsubstituted or mono- to tetrasubstituted aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, which may contain one or two substituents from the group comprising C.sub.1 -C.sub.3 haloalkyl having 1 to 7 halogen atoms, cyclopropyl, halocyclopropyl having 1 to 3 halogen atoms, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, C.sub.2 -C.sub.3 haloalkenyl and C.sub.2 -C.sub.3 haloalkynyl having 1 to 4 halogen atoms, C.sub.1 -C.sub.3 haloalkoxy having 1 to 7 halogen atoms, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 haloalkylthio having 1 to 7 halogen atoms, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro and one to four substituents from the group comprising C.sub.1 -C.sub.3 alkyl, C.sub.
    Type: Grant
    Filed: October 16, 1991
    Date of Patent: September 14, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Maienfisch, Odd Kristiansen, Laurenz Gsell
  • Patent number: 5240924
    Abstract: An N-acylamino acid derivative of the formula: ##STR1## wherein the substituents are herein defined, or a salt thereof, which is useful as hypotensive drugs.
    Type: Grant
    Filed: December 31, 1991
    Date of Patent: August 31, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hajime Morishima, Yutaka Koike, Masato Nakano, Shugo Atsuumi, Seiichi Tanaka, Kenji Matsuyama
  • Patent number: 5234946
    Abstract: The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7,X and Y are linking groups,R.sup.2 is H or lower alkyl,R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl,R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms,R.sup.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: August 10, 1993
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Hiroshi Takezawa, Masahiro Hayashi, Yoshikazu Iwasawa, Masaaki Hosoi, Yoshiaki Iida, Yoshimi Tsuchiya, Masahiro Horie, Toshio Kamei
  • Patent number: 5231109
    Abstract: Novel fungicides of the formula ##STR1## in which R.sup.1 represents optionally substituted hydroxyalkyl, optionally substituted hydroxyalkoxyalkyl, optionally substituted heteroarylalkyl or optionally substituted heteroaryl, andR.sup.2 represents optionally substituted alkyl, optionally substituted alkenyl, or alkinyl.Intermediates therefor, wherein R.sup.2 is hydrogen or an alkali metal cation, are also new.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: July 27, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Klaus Jellch, Winfried Lunkenhelmer, Wilhelm Brandes, Gerd Hanssler
  • Patent number: 5227392
    Abstract: An alkoxycoumarin substituted by a heterocyclic radical, or the formula ##STR1## R.sup.1 and R.sup.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, trifluoromethyl, phenyl or halogen, or together form a C.sub.3 -C.sub.5 -alkylene chain, R.sup.3 is C.sub.1 -C.sub.5 -alkyl or halogen, n is an integer of from 0 to 3, R.sup.4 is hydrogen or C.sub.1 -C.sub.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: July 13, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Fritz-Frieder Frickel, Thomas Kuekenhoehner, Beatrice Rendenbach-Mueller, Harald Weifenbach, Hans-Juergen Teschendorf
  • Patent number: 5225548
    Abstract: Indophenol dyes of the formula ##STR1## where X is nitrogen or the radical CH,Q is a five-membered heterocyclic radical, andK is a radical of an aniline, aminonaphthalene, aminoquinoline or aminothiazole derivative, andthe radical A can be benzofused,are useful for thermal transfer processes.
    Type: Grant
    Filed: September 20, 1991
    Date of Patent: July 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Bach, Karl-Heinz Etzbach, Ruediger Sens
  • Patent number: 5223616
    Abstract: A heterocyclic compound which is useful for dyeing or printing hydrophobic fiber materials and which has the following formula (I), ##STR1##wherein A.sub.1, A.sub.2, A.sub.3 and A.sub.4 are each hydrogen, halogen, alkyl, alkoxy or alkenyl, X.sub.1 is --O-- or the like, R.sub.1 is a methylene or the like, X.sub.2 is a direct linkage or a divalent group of --O--, --S--, --SO--, --SO.sub.2 --, ##STR2## in which R.sub.3 is a hydrogen atom or a C.sub.1-4 alkyl group, ##STR3## in which R.sub.3 is as defined above, T and u are each independently hydrogen or a C.sub.1-4 alkyl, l is O or an integer of 1 to 3, Q is an unsubstituted or substituted 5-, 6- or 7-membered saturated or unsaturated heterocyclic residue, Y is hydrogen, C.sub.1-4 alkyl, a C.sub.1-4 alkoxy group or the like.
    Type: Grant
    Filed: November 4, 1991
    Date of Patent: June 29, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
  • Patent number: 5213709
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 respectively denote an alkyl group having 1-16 carbon atoms optionally substituted; X.sub.1 and X.sub.3 respectively denote a single bond, --O--, ##STR2## X.sub.2 denotes a single bond, ##STR3## A.sub.1 denotes a single bond ##STR4## A.sub.3 denotes ##STR5## A.sub.2 denotes 9, 10-dihydro-2,7-phenanthrenediyl, 2,7-fluorenediyl or 2,7-fluorenonediyl; n is 0 or 1; and X.sub.4 and X.sub.5 respectively denote hydrogen, F, Cl, Br, --CH.sub.3, --CN or --CF.sub.3, with proviso that X.sub.1 is a single bond when A.sub.1 is a single bond.
    Type: Grant
    Filed: April 30, 1991
    Date of Patent: May 25, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Yoko Yamada, Shinichi Nakamura
  • Patent number: 5212189
    Abstract: The present invention is a novel compound which is a thiadiazole or oxadiazole analog of a fenamic acid having a substituted hydroxamate side chain and pharmaceutically acceptable acid addition or base salts thereof, pharmaceutical compositions and methods of use thereof. The invention compounds are now found to have activity as inhibitors of one or both of cyclooxygenase and 5-lipoxygenase providing treatment of conditions advantageously affected by such inhibition including inflammation, arthritis, pain, fever, and the like. Thus, the present invention is also a pharmaceutical composition or method of use thereof.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: May 18, 1993
    Assignee: Warner-Lambert Company
    Inventors: Thomas R. Belliotti, David T. Connor, Catherine R. Kostlan
  • Patent number: 5209866
    Abstract: Heterocyclic 1,2-difluorobenzene derivatives of the formula I ##STR1## in which R.sup.1 and R.sup.2, in each case independently of one another, are an alkyl groups (sic) having 1-15 C atoms in which, in addition, one or more CH.sub.2 groups may be replaced by a divalent radical selected from the group comprising --O--, --S--, --CO--, --O--CO--, --CO--O--, --CH.dbd.CH-- and --C.tbd.C--, where two heteroatoms are not linked directly to one another,A.sup.1 and A.sup.2, in each case independently of one another, are a 1,4-phenylene group which is unsubstituted or monosubstituted or polysubstituted by fluorine, and in which, in addition, one or two CH groups may be replaced by N, or are a 1,3,4-thiadiazole-2,5-diyl group or a trans-1,4-cyclohexylene group,m and n are each 0 or 2,o is 0 or 1, andp is 0, 1 or 2,where (o+p) is 1, 2 or 3 and, in the case where p=2, the A.sup.2 groups and n may be identical or different with the proviso that at least one of the groups A.sup.1 and A.sup.
    Type: Grant
    Filed: May 15, 1989
    Date of Patent: May 11, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Volker Reiffenrath, Joachim Krause, Andreas Wachtler, Thomas Geelhaar
  • Patent number: 5210204
    Abstract: Heterocyclic methyl derivatives of biphenyl oxadiazoles and thiadiazoles are described, as well as methods for the preparation of said derivatives and pharmaceutical compositions of the same, which are useful as antagonists of the angiotensin II enzyme and thus useful in treating hypertension, hyperaldosteronism, congestive heart failure, and glaucoma.
    Type: Grant
    Filed: June 16, 1992
    Date of Patent: May 11, 1993
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Catherine R. Kostlan
  • Patent number: 5207816
    Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is alkyl, R.sup.2 is alkyl, unsubstituted or halogen-substituted alkenyl or alkynyl, X is a substituted or unsubstituted five-membered heteroaromatic radical, and Z is hydrogen, methoxycarbonyl, ethoxycarbonyl, methyl or cyano, processes for their manufacture, and the use of these compounds for controlling undesirable plant growth.
    Type: Grant
    Filed: June 6, 1991
    Date of Patent: May 4, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
  • Patent number: 5205853
    Abstract: Herbicidal sulphonylated carboxamides of the formulaR.sup.1 --CO--NH--SO.sub.2 --(A).sub.n --R.sup.2 (I)in whichn represents the numbers 0 or 1,A represents oxygen, imino (NH) or methylene (CH.sub.2),R.sup.1 represents a five-membered heteroaryl radical which contains 1 or 2 nitrogen atoms and additionally one oxygen or sulphur atom in the ring and which is optionally substituted by halogen or by alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or phenyl which are in each case optionally substituted, andR.sup.2 represents aryl or heteroaryl which are in each case optionally substituted,or salts thereof, with the exclusion of the compound 2-dimethylamino-N-(4-methyl-phenylsulphonyl)-5-thiazole carboxamide.
    Type: Grant
    Filed: May 23, 1991
    Date of Patent: April 27, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
  • Patent number: 5202345
    Abstract: A compound of the formula: ##STR1## wherein R.sup.1 is hydrogen, or C.sub.1 14 C.sub.6 alkyl; n is an integer of from 2 to 3; Z.sup.1 is phenyl, benzyl, or isoxazolyl and each is optionally substituted by a halogen, a methoxy, or a methyl group; Z.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, allyl, unsubstituted phenyl, or phenyl substituted by halogen, methyl, or methoxy; orZ.sub.1 and Z.sub.2 are taken together with the adjacent nitrogen atom to form triazolyl, imidazolyl or pyrazolyl; or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: February 7, 1992
    Date of Patent: April 13, 1993
    Assignee: Shionogi & Co., Ltd.
    Inventors: Hiromu Matsumura, Toshisada Yano, Akira Matsushita, Masami Eigyo
  • Patent number: 5200109
    Abstract: A mesomorphic compound represented by the following formula (I): ##STR1## wherein R.sub.1 and R.sub.2 respectively denote a linear or branched alkyl group having 1-18 carbon atoms capable of including one or non-neighboring two or more methylene groups which can be replaced with at least one species of --O--, --S--, --CO--, --COO--, --OCO-- and --OCOO--; ##STR2## and n is 0 or 1.
    Type: Grant
    Filed: January 15, 1992
    Date of Patent: April 6, 1993
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takashi Iwaki, Takao Takiguchi, Shinichi Nakamura, Yoko Yamada, Takeshi Togano, Shosei Mori
  • Patent number: 5194167
    Abstract: Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives have been found to be effective antioxidant and antiwear additives for lubricants and fuels.
    Type: Grant
    Filed: May 8, 1991
    Date of Patent: March 16, 1993
    Assignee: Mobil Oil Corporation
    Inventors: Shih-Ying Hsu, Andrew G. Horodysky
  • Patent number: 5190963
    Abstract: Cyclopropane(thio)carboxamides of the general formula I ##STR1## where the index and the substituents have the following meanings: n is 0, 1 or 2, it being possible for the R.sup.2 radicals to be different when n is 2;A.sup.1 and A.sup.2 are substituted or unsubstituted alkylene;R.sup.1 is hydrogen, halogen or alkyl;R.sup.2 is halogen or alkyl;X is substituted or unsubstituted 5-membered heteroaryl, substituted or unsubstituted pyrazolyl-1-oxy or triazolyl-1-oxy; andY is oxygen or sulfur,processes for their manufacture, intermediates therefor, and the use of compounds I.
    Type: Grant
    Filed: February 3, 1992
    Date of Patent: March 2, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Nuebling, Hans Theobald, Uwe Kardorff, Wolfgang Krieg, Christoph Kuenast
  • Patent number: 5169427
    Abstract: Herbicidal cycloalkyl-substituted thiadiazolyloxyacetamides of the formula ##STR1## in which R.sup.1 represents hydrogen, or represents an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkynyl and aralkyl,R.sup.2 represents an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkenyloxy and alkynyloxy, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form an optionally substituted saturated or unsaturated nitrogen-heterocyclic radical, which can contain further hetero atoms and to which a benzo grouping can be fused, andR.sup.3 represents optionally substituted cycloalkyl.Intermediates of the formula ##STR2## are also new.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: December 8, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Hans-Joachim Diehr, Bernd Baasner, Ernst Kysela, Albrecht Marhold, Karl-Rudolf Gassen, Robert R. Schmidt
  • Patent number: 5166216
    Abstract: Methyl .alpha.-arylacrylates substituted by a heterocyclic radical and having the general formula ##STR1## where R is alkyl, alkenyl, haloalkyl, cycloalkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, halogen or aryl, the aromatic ring being unsubstituted or substituted, Het is a five-membered heteroaromatic ring which is unsubstituted or substituted and has from one to three heteroatoms, and A is ethenylene, ethylene, methyleneoxy or methylenethio, and fungicides and pesticides containing these compounds.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Schuetz, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Ulrich Schirmer, Peter Hofmeister, Christoph Kuenast, Eberhard Ammermann, Gisela Lorenz, Uwe Kardorff
  • Patent number: 5162539
    Abstract: A process for the preparation of a 2-alkylthio-1,3,4-thiadiazole of the formula ##STR1## in which R.sup.1 represents alkyl which is optionally substituted by halogen andR.sup.2 represents alkyl or aralkyl,which comprises reacting a carboxylic acid of the formulaR.sup.1 --COOH (II),with a dithiocarbazic ester of the formula ##STR2## in the presence of phosphoryl chloride (POCl.sub.3) at a temperature between -20.degree. C. and +120.degree. C.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: November 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Joachim Diehr
  • Patent number: 5162349
    Abstract: Mercapto-bis-[1,3,4-oxa- and -thiadiazoles] ##STR1## in which X.sub.1 and X.sub.2 independently of one another are oxygen or sulfur, R.sub.1 is hydrogen or C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkoxy or cyano; C.sub.3 -C.sub.7 alkenyl which is unsubstituted or substituted by halogen; or C.sub.3 -C.sub.7 alkynyl which is unsubstituted or substituted by halogen,R.sup.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.3 alkoxy which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkylthio which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.7 alkenylthio which is unsubstituted or substituted by halogen, C.sub.3 -C.sub.7 alkylnylthio which is unsubstituted or substituted by halogen, --SH, phenyl which is unsubstituted or substituted by halogen or ##STR2## in which R.sub.3 and R.sub.4 are C.sub.1 -C.sub.3 alkyl, and processes for the preparation of the compounds of the formula I are described.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: November 10, 1992
    Assignee: Ciba-Geigy Corporation
    Inventors: Ernst Beriger, Wolfgang Eckhardt