Chalcogen Bonded Directly To Ring Carbon Of The Oxadiazole Ring Patents (Class 548/144)
  • Patent number: 5496835
    Abstract: This invention relates to a compound represented by the formula ##STR1## wherein the ring A stands for a 5-10 membered aromatic heterocyclic group optionally having, besides R.sup.1 and R.sup.2, further substituents; R.sup.1 stands for an optionally substituted hydrocarbon residue which is optionally bonded through a hetero-atom; R.sup.2 stands for a group capable of liberating proton in a living body or a group convertible thereinto; R.sup.
    Type: Grant
    Filed: December 22, 1993
    Date of Patent: March 5, 1996
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Keiji Kubo, Yoshiyuki Inada, Takehiko Naka
  • Patent number: 5484763
    Abstract: There are provided substituted benzisoxazole and benzisothiazole compounds having the structural formula I ##STR1## Further provided are compositions and methods comprising those compounds for the control of undesirable plant species.
    Type: Grant
    Filed: February 10, 1995
    Date of Patent: January 16, 1996
    Assignee: American Cyanamid Company
    Inventor: Peter J. Wepplo
  • Patent number: 5482966
    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: June 13, 1994
    Date of Patent: January 9, 1996
    Assignees: Zeneca Limited, Zeneca Pharma S.A.
    Inventors: Thomas G. C. Bird, Patrick Ple
  • Patent number: 5462952
    Abstract: The present invention is novel compounds which are 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, and pharamaceutically acceptable acid addition or base salts thereof having activity as inhibitors of singly or together 5-lipoxygenase and cyclooxygenase, and pharmaceutical compositions or methods of use therefor.
    Type: Grant
    Filed: September 8, 1993
    Date of Patent: October 31, 1995
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Milton L. Hoefle
  • Patent number: 5438066
    Abstract: Fungicidal and insecticidal compounds having the general formula (I): ##STR1## or a stereoisomer thereof, wherein A is CH or N; B is OCH.sub.3 or NHCH.sub.3 ; one of L and M is N and the other is S or O; X is an optionally substituted carbocyclic or heterocyclic group; and n is 0 or 1.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: August 1, 1995
    Assignee: Zeneca Limited
    Inventor: Ian R. Matthews
  • Patent number: 5434267
    Abstract: Process for the preparation of compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2, R.sup.3, X and n have the meaning given in the description, by reacting acetates with carbon monoxide in the presence of a basic auxiliary, followed by alkylation. The products are intermediates for fungicidal acrylates.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: July 18, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
  • Patent number: 5418246
    Abstract: A description follows of oxa(thia)diazol- and triazol-ones(thiones), with a iticide and insecticide activity, having the general formula ##STR1## wherein: Y=0, S; Z=0, S, NCH.sub.3, one of the two substituents P and Q is an ortho-substituted phenyl and the other a substituted benzyl.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: May 23, 1995
    Assignee: Ministero Dell `Universita` E Della Ricerca Scientifica E Technologica
    Inventors: Franco Bettarini, Luigi Capuzzi, Piero La Porta, Sergio Massimini, Vincenzo Caprioli
  • 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: 5403851
    Abstract: This invention relates to novel substituted tryptamine and phenalkylamine and related compounds, pharmaceutical compositions thereof and methods of using said compounds and compositions for a number of pharmaceutical indications including (but not limited to): 1. central nervous system and psychiatric disorders (e.g., sleep disorders, epilepsy and other convulsive disorders, anxiety, psychiatric diseases, neurodegenerative diseases, fever); 2. chronobiological-based disorders (e.g., jet lag, delayed sleep syndrome, shift-work, seasonal affective disorder); 3. endocrine indications (e.g., contraception and infertility, precocious puberty, premenstrual syndrome, hyperprolactinemia, growth hormone deficiency); 4. cancer and other proliferative diseases; 5. immune system disorders and conditions associated with senescence; 6. ophthalmological diseases; 7. animal breeding (e.g., regulation of fertility, puberty, pelage color).
    Type: Grant
    Filed: April 5, 1994
    Date of Patent: April 4, 1995
    Assignee: Interneuron Pharmaceuticals, Inc.
    Inventors: Kay J. D'Orlando, Kenneth W. Locke, Emile M. Bellott, Richard L. Gabriel, Michael D. Nohrden, Yesh P. Sachdeva, Salah A. Zahr, Emile Al-Farhan, Subramaniam Krishnananthan
  • Patent number: 5391561
    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 diclosed to useful as antimicrobials.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: February 21, 1995
    Assignee: Rohm and Haas Company
    Inventor: Adam C.-T. Hsu
  • Patent number: 5391560
    Abstract: The invention relates to new substituted carbamoylpyrazolines ##STR1## to processes in their preparation, and to their use as pesticides.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: February 21, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rainer Fuchs, Johannes Kanellakopulos, Christoph Erdelen, Wilhelm Stendel
  • Patent number: 5376648
    Abstract: Derivatives having the formula: ##STR1## in which R.sub.1 =C.sub.1 -C.sub.4 alkyl and Ar is an aryl or heteroaryl group chosen from among the following: ##STR2## where R.sub.2 represents a hydrogen atom one or two halogen atoms, a CN, NO.sub.2 or CF.sub.3 group, one, two or three C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups or an amino group substituted by two C.sub.1 -C.sub.4 alkyl groups, in which case the --W--V-- chain represents --N.dbd.N-- or ##STR3## and n=2-6; (ii) pyridyl, in which case the --W--V-- chain represents --N.dbd.N-- and n= 1-6, and acid addition salts of those derivatives (I) which are salt-forming.These derivatives are of use in therapy as agents for inhibiting type B monoamine oxydase.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: December 27, 1994
    Assignee: Delalande S.A.
    Inventors: Jean-Jacques Koenig, Luc L. Lebreton, Maryse F. Masson
  • 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: 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: 5324709
    Abstract: A tetrahydrofuran derivative represented by the following general formula [I]: ##STR1## wherein A represents direct bonding or a group represented by --B--CHR.sup.1 --(wherein B represents oxygen atom, sulfur atom or imino group; R.sup.1 represents hydrogen atom or an alkyl group); R represents hydrogen atom, halogen atom, hydroxyl group, an alkoxy group, benzyloxy group, an alkylsulfonyloxy group or a group represented by --O--COR.sup.2 (wherein R.sup.2 represents an alkyl group, a haloalkyl group, an alkenyl group, a cycloalkyl group, phenyl group, benzyl group, an alkoxy group, an alkylamino group or a dialkylamino group; X represents halogen atom; Y represents hydrogen atom or halogen atom) and the herbicide containing the same as the effective ingredient. The compounds of the present invention have exceedingly high herbicidal activity, and furthermore, the compounds are superior to the known similar compounds in terms of safety on crops. Thus, the compounds are useful as herbicides.
    Type: Grant
    Filed: November 20, 1992
    Date of Patent: June 28, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Natsume Bunji, Kyomura Nobuo, Suzuki Seiichi, Takahashi Yoji, Jikihara Tetsuo
  • Patent number: 5324837
    Abstract: 3,4-Diaryl-4,5-dihydro-1H-pyrazole compounds having a selected 5- or 6-membered aromatic heterocyclic moiety in the 4-position and an optionally substituted phenyl moiety in the 3-position, such as 4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazo le were prepared as intermediates in the preparation of insecticidal 3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds. The 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds can be prepared from appropriate 1,2-diarylethanone compounds by successive treatments with N,N,N',N'-tetramethyldiaminomethane in dichloromethane in the presence of acetic anhydride (to form a Mannich adduct) and hydrazine in the presence of a catalytic amount of trifluoroacetic acid.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: June 28, 1994
    Assignee: DowElanco
    Inventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
  • Patent number: 5294596
    Abstract: The invention relates to novel heterocyclyltriazolinones of the general formula (I) ##STR1## in which R.sup.1 represents hydrogen or represents alkyl or cycloalkyl, each of which is optionally substituted,R.sup.2 represents hydrogen, hydroxyl, mercapto or halogen or represents alkyl, alkenyl, alkinyl, cycloalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, arylalkyl, amino or heterocyclyl, each of which is optionally substituted, andHet represents an optionally substituted heterocycle of the formula ##STR2## in which X in each case represents oxygen, sulphur, an NH group or an N-alkyl group,a process for their preparation and their use as herbicides.
    Type: Grant
    Filed: July 21, 1993
    Date of Patent: March 15, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Haas, Kurt Findeisen, Karl-Heinz Linker, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
  • Patent number: 5283340
    Abstract: A photographic naphtholic coupler comprising a ballast free naphtholic coupler moiety containing a --CONH.sub.2 group in the 2- position and a ballasted coupling-off group in the 4- position enables good wash out of dye formed upon oxidative coupling from a photographic material during processing of such a photographic material. Such a naphtholic coupler is useful in photographic silver halide materials and processes.
    Type: Grant
    Filed: June 4, 1992
    Date of Patent: February 1, 1994
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Teh-hsuan Chen, Hans G. Ling, John W. Harder, Arlyce T. Bowne
  • 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: 5274102
    Abstract: Epoxy functional copolymers of a higher .alpha.-olefin, and an unsaturated dicarboxylic acid ester formed by copolymerization of olefin, acid ester and ethylenically unsaturated glycidyl compound can be used to form nitrogen, oxygen, phosphorus and/or sulfur-containing lubricant additives by reaction of the epoxy functionality in such a copolymer with glycidyl-reactive compounds containing nitrogen, oxygen, phosphorus and/or sulfur atoms. Alternatively, the copolymerization reaction can utilize the olefin, unsaturated acid ester, and an ethylenically unsaturated compound containing the nitrogen, phosphorus and/or sulfur atom, which compound is formed by reaction of ethylenically unsaturated glycidyl compound and an epoxy-reactive nitrogen, phosphorus, and/or sulfur-containing compound.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: December 28, 1993
    Assignee: Akzo nv
    Inventors: Theodore A. Marolewski, Eric W. Burkhardt, Uwe H. Wallfahrer
  • Patent number: 5268375
    Abstract: This invention relates to compounds of formula ##STR1## in which: R.sub.1 and R.sub.2 are similar or different and are each independently hydrogen or a group selected from CO.sub.2 N.dbd.C(NH.sub.2).sub.2, CONHNHCONH.sub.2, CONHNHCSNH.sub.2, C(OC.sub.2 H.sub.5).dbd.NCO.sub.2 CH.sub.3, COCH.sub.2 CO.sub.2 H.sub.5, N(OH)-CONHCOOC.sub.2 NCO.sub.2 CH.sub.3, COCH.sub.2 CO.sub.2 H.sub.5, N(OH)-CONHCOOC.sub.2 H.sub.5, C(OC.sub.2 H.sub.5).dbd.NH or a nitrogen heterocycle; with the proviso that at least one of the substituents R.sub.1 or R.sub.2 is other than hydrogen;R.sub.3 is a hydrogen, a C.sub.1 -C.sub.6 alkyl, a C.sub.2 -C.sub.6 alkenyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl, a phenylalkyl, or a phenylalkenyl;R.sub.4 and R.sub.5 are each independently a C.sub.1 -C.sub.6 alkyl, a C.sub.3 -C.sub.7 cycloalkyl, a phenyl or a phenylalkyl; orR.sub.4 and R.sub.5, bonded together, are either a group of the formula (CH.sub.2).sub.n or a group of the formula (CH.sub.2).sub.p Y (CH.sub.2).sub.
    Type: Grant
    Filed: February 28, 1992
    Date of Patent: December 7, 1993
    Assignee: Elf Sanofi
    Inventors: Claude Bernhart, Bernard Ferrari, Pierre Perreaut
  • 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: 5250551
    Abstract: Compounds for therapeutic use of formula: ##STR1## where the chain--W--V--N--represents--N.dbd.N--N--, --N--N.dbd.N--,--O--CO--N--,--O--CS--N--, --S--CO--N--or--S--CS--N--; Ar is an aryl group; and A is a vinyl group or an alkylene chain terminated by CN, methoxy, ethoxy, OH, halogen or NH.sub.2 which may possibly be substituted.
    Type: Grant
    Filed: January 3, 1992
    Date of Patent: October 5, 1993
    Assignee: Delalande S.A.
    Inventors: Rene L. Milcent, Luc Lebreton, Fathi Mazouz, Claude Burstein, Salah Gueddari
  • Patent number: 5240947
    Abstract: The present invention provides a novel series of 2,3,4,5-substituted furo[2,3-c]pyrazole compounds. These compounds are found potent in inhibiting thrombocyte aggregation and antiallergy effect.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: August 31, 1993
    Assignee: National Science Council
    Inventors: Sheng-Chu Kuo, Li-Jiau Huang, Che-Ming Teng
  • Patent number: 5236939
    Abstract: Substituted 1,3,4 -oxa- diazolinones of the formula (I) ##STR1## in which X represents O andY represents O or S,are disclosed as useful to combat endoparasites.
    Type: Grant
    Filed: October 17, 1991
    Date of Patent: August 17, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Nikolaus Muller, Achim Harder
  • 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: 5221684
    Abstract: Hydroquinone diethers of the formula I ##STR1## where A.sup.1 and A.sup.2 are substituted or unsubstituted alkylene;R.sup.1 is hydrogen, halogen or alkyl;R.sup.2 is substituted or unsubstituted pyrazolyl or pyridyl;X is a substituted or unsubstituted 5-membered heteroaromatic radical, are prepared as described using the described intermediates, and are used as pesticides.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: June 22, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christoph Nuebling, Hans Theobald, Wolfgang Krieg, Uwe Kardorff, Christoph Kuenast
  • 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: 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: 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: 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
  • Patent number: 5124341
    Abstract: The present invention relates to an oxadiazolinone derivative represented by the following general formula, a process for producing the same and insecticides containing the same as an active ingredient: ##STR1## wherein R.sup.1 is a haloalkyl group or a haloalkoxy group; R.sup.2 is a halogen atom, nitro group, trifluoromethyl group of 1-pyrrolyl group; R.sup.3 is a bicycloalkyl group, a methyl- or choro-substituted cycloalkyl group, an alkenyl group, a methyl-substituted cycloalkenyl group, 2-methyl-1,3-dithioran-2-yl group or an alkyl group, wherein the alkyl group may be substituted with a halogen atom, an alkoxy group, an alkylthio group, an alkylsulfinyl group, an alkylsulfonyl group or an alkoxycarbonyl group; R.sup.4 is hydrogen atom or fluorine atom; and X is CR.sup.2 or N.The oxidiazolinone derivative can be used as an insecticide by formulating it into emulsifiable concentrates, wettable powders, dusts, granules, flowable concentrates and poison baits, etc..
    Type: Grant
    Filed: December 18, 1990
    Date of Patent: June 23, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroki Tomioka, Noriyasu Sakamoto, Kimitoshi Umeda, Hiroaki Fujimoto, Takao Ishiwatari, Hirosi Kisida
  • Patent number: 5102897
    Abstract: The novel 3,5-ditertiarybutyl-4-hydroxyphenylthio-1,3,4-thiadiazoles and oxadiazoles and 3,5-ditertiarybutyl-4-hydroxyphenylmethanone-1,3,4-thiadiazoles and oxadiazoles and related compounds of the present invention are antiinflammatory agents having activity as inhibitors of 5-lipoxygenase, cyclooxygenase or both.
    Type: Grant
    Filed: January 24, 1991
    Date of Patent: April 7, 1992
    Assignee: Warner-Lambert Company
    Inventors: Diane H. Boschelli, David T. Connor, Catherine R. Kostlan, James B. Kramer, Michael D. Mullican, Jagadish C. Sircar
  • Patent number: 5101034
    Abstract: A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, andR.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, halogenoalkyl, alkoxyalkyl, alkoxy, aralkyl or aryl, orR.sup.1 and R.sup.2, together with the nitrogen atom to which they are bonded, form a heterocycle,which comprises reacting a sulphonylated heteroaromatic of the formulaR--SO.sub.2 --R'in whichR' is lower alkyl or benzyl,with an .alpha.-oxyacetamide of the formula ##STR2## in which R" is hydrogen or acyl,in the presence of an inorganic base as an acid acceptor and of solvent as a diluent at a temperature of about -50.degree. C. to +150.degree. C. The products are known herbicides.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: March 31, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Schmidt, Hans-Joachim Diehr
  • Patent number: 5093343
    Abstract: Substituted 1,3,4-oxa- and thiadiazolinones of the formula (I) ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkoxy, alkylthio, halogen, halogenoalkyl, halogenoalkoxy or halogenoalkylthio,R.sup.2 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.2, NH.sub.2, alkylamino, dialkylamino, alkylcarbonyl, carbalkoxy, alkylsulphonyl, arylsulphonyl, sulphamoyl, alkylsulphamoyl, dialkylsulphamoyl, aryl, aryloxy or arylthio, which, in turn, can be sutstituted,R.sup.3 represents one or more identical or different radicals from among hydrogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylenedioxy, halogenoalkylenedioxy, halogen, CN, NO.sub.
    Type: Grant
    Filed: September 5, 1990
    Date of Patent: March 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Nikolaus Muller, Achim Harder
  • Patent number: 5064845
    Abstract: This invention relates to the use of iodopropargyl compounds invention have the structure ##STR1## wherein A is hydrogen, alkyl, cycloalkyl, alkenyl, alkynyl, phenyl, phenylalkyl, naphthyl or heterocyclyl; andZ is oxygen (O) or N--R;wherein R is hydrogen, alkyl, cycloalkyl, phenyl, or phenylalkyl as agricultural fungicides and to agricultural fungicidal compositions containing the iodopropargyl compounds.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: November 12, 1991
    Assignee: Rohm and Haas Company
    Inventors: Adam C. Hsu, Daniel L. Loughner
  • Patent number: 5053071
    Abstract: This invention pertains to novel heterocyclic 2,3-dihydrobenzofuran and chromane compounds, including stereoisomers, agriculturally suitable compositions containing them, and their use as broad spectrum herbicides.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: October 1, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph E. Semple
  • Patent number: 5034151
    Abstract: There is disclosed a mesomorphic compound represented by the following formula (I): ##STR1## wherein A.sub.1 denotes a single bond, ##STR2## denotes ##STR3## X denotes hydrogen, a halogen or cyano group; Y denotes oxygen or sulfur; R.sub.1 and R.sub.2 respectively denotes a linear or branched alkyl, alkoxy, alkylcarbonyloxy, alkoxycarbonyl or alkoxycarbonyloxy group each having 1-18 carbon atoms and each capable of having a substituted of chloro, bromo, cyano, alkoxy or akoxycarbonyl group; and B denotes ##STR4## A ferroelectric liquid crystal composition comprises at least two mesomorphic compounds including at least one mesomorphic compound represented by the formula (I). A ferroelectric liquid crystal device is constituted by disposing the ferroelectric liquid crystal composition between a pair of substrates.
    Type: Grant
    Filed: March 27, 1989
    Date of Patent: July 23, 1991
    Assignee: Canon Kabushiki Kaisha
    Inventors: Kenji Shinjo, Akio Yoshida, Takashi Iwaki, Takao Takiguchi, Hiroyuki Kitayama, Kazuharu Katagiri
  • Patent number: 5013745
    Abstract: 2-Mercapto-1,3,4-oxadiazoles and 2-mercapto-1,3,4-thiadiazoles of the formula I ##STR1## in which X.sub.1 and X.sub.2 independently of one another are oxygen or sulfur, R.sub.1 is difluoromethyl or 3,4,4-trifluoro-3-butenyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl and R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkenyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkynyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, or phenyl which is unsubstituted or substituted by halogen, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 alkoxy, or wherein, furthermore, R.sub.2 and R.sub.3 together can form the methylene chain (--CH.sub.2 --)n as a constituent of a 5- or 6-membered ring with the heteroatom X.sub.1, in which n is 3 or 4, and processes for the preparation of the compounds of the formula I are described.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: May 7, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Ernst Beriger, Wolfgang Eckhardt
  • Patent number: 4988706
    Abstract: Novel compounds of formula (I), processes for their preparation, and their use as pharmaceutical agents are described: ##STR1## in which X represents a group ##STR2## wherein one of Y and Z represents nitrogen and the other represents CR where R is selected from halogen, CN, OR.sup.1, SR.sup.1, N(R.sup.1).sub.2, NHR.sup.1, NHCOR.sup.1, NHCOOCH.sub.3, NHCOOC.sub.2 H.sub.5, NHOR.sup.1, NHNH.sub.2, COR.sup.1, COR.sup.2, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl or C.sub.1-2 alkyl substituted with OR.sup.1, N(R.sup.1).sub.2, SR.sup.1, CO.sub.2 R.sup.1, CON(R.sup.1).sub.2 or one or two halogen atoms, in which R.sup.1 is hydrogen or C.sub.1-2 alkyl and R.sup.2 is OR.sup.1, NH.sub.2 or NHR.sup.1 ; and each of p and q independently represents an integer of 2 to 4.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: January 29, 1991
    Assignee: Beecham Group P.L.C.
    Inventors: Michael S. Hadley, Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
  • Patent number: 4952580
    Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 28, 1990
    Assignee: FMC Corporation
    Inventors: Anthony J. Martinez, Thomas G. Cullen
  • Patent number: 4952599
    Abstract: Novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.10 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl which is substituted by one or more halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups; C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl, di(C.sub.3 -C.sub.8)cycloalkyl-C.sub.1 -C.sub.4 alkyl; C.sub.1 -C.sub.4 phenylalkyl or C.sub.1 -C.sub.4 phenylalkyl which is substituted in the phenyl nucleus by one or more members selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and/or C.sub.1 -C.sub.4 haloalkyl; or is C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.3 alkyl,R.sub.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: August 28, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
  • Patent number: 4948418
    Abstract: This invention pertains to novel heterocyclic 2,3-dihydrobenzofuran and chromane compounds, including stereoisomers, agriculturally suitable compositions containing them, and their use as broad spectrum herbicides.
    Type: Grant
    Filed: August 30, 1989
    Date of Patent: August 14, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Joseph E. Semple
  • Patent number: 4943584
    Abstract: Novel (p-phenoxyphenoxy)-methyl-five-membered heeroaromatic radicals of the formula ##STR1## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3 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,R.sup.4 hydrogen or C.sub.1 -C.sub.4 -alkyl, and a five-membered heteroaromatic ring, and their use for combating pests.
    Type: Grant
    Filed: April 20, 1988
    Date of Patent: July 24, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
  • Patent number: 4943583
    Abstract: The invention is concerned with novel compounds of the formula ##STR1## wherein R.sup.1 signifies optionally substituted phenyl or pyridyl, R.sup.2 signifies substituted phenyl, X signifies oxygen, sulfur or NR.sup.3, Y signifies oxygen or sulfur and R.sup.3 signifies methyl, halomethyl or 2-propynyl, and their manufacture, pest control compositions which contain said compounds as the active ingredient and the use of the active substances or compositions for the control of pests.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: July 24, 1990
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Christoph Luthy
  • Patent number: 4912225
    Abstract: A compound of the formula: ##STR1## wherein A is a nitrogen-containing group selected from the group consisting of --NO.sub.2, --NH.sub.2, --N.dbd.C(NH.sub.2)--S--, and --NH--CO--S; X is a fluorine atom or a chlorine atom; and R.sup.2 is a t-butyl group or a 1-methylcyclopropyl group. These compounds are useful as intermediates in the production of herbicidal benzothiazolone compounds.
    Type: Grant
    Filed: October 4, 1988
    Date of Patent: March 27, 1990
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Haga, Eiki Nagano, Ryo Sato, Kouichi Morita
  • Patent number: 4906628
    Abstract: Phosphodiesterase (type III) inhibitors having the formula: ##STR1## which are useful in stimulating cardiac activity and in treating congestive heart failure and bronchoconstriction, pharmaceutical compositions including these inhibitors, and methods of using these compounds to produce phosphodiesterase (type III) inhibition in mammals.
    Type: Grant
    Filed: October 14, 1986
    Date of Patent: March 6, 1990
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: William J. Coates
  • Patent number: 4888348
    Abstract: The invention relates to novel substituted phenylthioureas, phenylisothioureas and phenylcarbodiimides of formula I ##STR1## wherein Z is ##STR2## or --N.dbd.C.dbd.N--; R.sub.1 is C.sub.1 -C.sub.12 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.3 alkyl substituted by 1 or 2 C.sub.3 -C.sub.6 cycloalkyl radicals, or is alkoxyalkyl containing a total of 3 to 10 carbon atoms, halogen-substituted C.sub.1 -C.sub.12 alkyl, polycyclic C.sub.7 -C.sub.10 cycloalkyl, or phenyl(C.sub.1 -C.sub.5)alkyl which may be substituted in the phenyl moiety by 1 or 2 identical or different members selected from the group consisting of halogen, methoxy, ethoxy and C.sub.1 -C.sub.5 alkyl,R.sub.2 is hydrogen or C.sub.1 -C.sub.5 alkyl,R.sub.3 is C.sub.1 -C.sub.5 alkyl or C.sub.3 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: December 19, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson