Chalcogen Bonded Directly To Ring Carbon Of The Thiadiazole Ring Patents (Class 548/129)
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Patent number: 5464866Abstract: Substituted hydrindanes and their use in controlling angiogenesis-dependent diseases in warm blooded animals are disclosed.Type: GrantFiled: March 10, 1994Date of Patent: November 7, 1995Assignee: Alcon Laboratories, Inc.Inventors: Abbot F. Clark, Raymond E. Conrow
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Patent number: 5453433Abstract: Compounds of the formula; ##STR1## wherein: Thi is thiadiazolyl or substituted thiadiazolyl;Y is alkylene bridge of 3-9 carbon atoms;R.sub.1 and R.sub.2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinyl alkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl, or cyano;R.sub.3 is alkoxycarbonyl, phenyl, alkyltetrazolyl, or heterocyclyl; or a pharmaceutically acceptable salt thereof are effective antipicornaviral agents.Type: GrantFiled: May 13, 1994Date of Patent: September 26, 1995Assignee: Sterling Winthrop Inc.Inventors: David J. Aldous, Thomas R. Bailey, Guy D. Diana, Theodore J. Nitz
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Patent number: 5438066Abstract: 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: GrantFiled: October 27, 1993Date of Patent: August 1, 1995Assignee: Zeneca LimitedInventor: Ian R. Matthews
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Patent number: 5434267Abstract: 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: GrantFiled: March 14, 1994Date of Patent: July 18, 1995Assignee: Bayer AktiengesellschaftInventors: Helmut Kraus, Alexander Klausener, Hans-Joachim Diehr
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Patent number: 5409944Abstract: 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: GrantFiled: March 12, 1993Date of Patent: April 25, 1995Assignee: Merck Frosst Canada, Inc.Inventors: W. Cameron Black, Chun-Sing Li, Daniel Guay, Petpiboon Prasit, Patrick Roy
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Patent number: 5384070Abstract: The use of optically active tetrahydrofuran-2-carboxylic acid esters as dopants in liquid-crystal mixtures, liquid-crystal mixtures containing same and novel optically active tetrahydrofuran-2-carboxylic acid esters.Optically active tetrahydrofuran-2-carboxylic acid esters containing a mesogenic molecular building unit are suitable as dopants in liquid-crystal mixtures. They result in liquid-crystalline ferroelectric phases having short switching times and in electroclinic phases having large electroclinic coefficients. A further advantage is that they induce a helix having a very small pitch so that they are also suitable for helix compensation in LC mixtures.The compounds are symbolized by the general formula: ##STR1## in which the symbols and indices essentially denote: R.sup.1 =alkyl/alkenyl or tetrahydrofurancarbonyloxy or -thio; j, l, n=zero, 1 or 2; k, m=zero or 1; --A.sup.1, --A.sup.2, --A.sup.3 =phenylene, cycloalkylene or corresponding heterocyclates containing nitrogen, oxygen or sulfur; --M.sup.Type: GrantFiled: May 20, 1993Date of Patent: January 24, 1995Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Hemmerling, Hans-Rolf Dubal, Claus Escher, Gerhard Illian, Yoshio Inoguchi, Ingrid Muller, Mikio Murakami, Dieter Ohlendorf, Rainer Wingen
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Patent number: 5336420Abstract: 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: GrantFiled: December 14, 1992Date of Patent: August 9, 1994Assignee: Mobil Oil CorporationInventors: Andrew G. Horodysky, Shih-Ying Hsu, Andrew Jeng, Leslie R. Rudnick
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Patent number: 5332757Abstract: 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: GrantFiled: February 8, 1993Date of Patent: July 26, 1994Assignees: Zeneca Limited, Zeneca PHARMA S AInventors: Thomas G. C. Bird, Patrick Ple
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Patent number: 5324837Abstract: 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: GrantFiled: August 17, 1992Date of Patent: June 28, 1994Assignee: DowElancoInventors: James M. Renga, Kevin L. McLaren, James T. Pechacek, Michael J. Ricks, Yulan C. Tong
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Patent number: 5322949Abstract: Fungicidal thiadiazole-substituted acrylic acid esters of the formula ##STR1## in which R.sup.1 represents hydrogen, unsubstituted or substituted alkyl or alkenyl, or in each case unsubstituted or substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents alkyl,R.sup.3 represents dialkylamino or a radical --Z--R.sup.4,Y represents oxygen, sulphur or a radical ##STR2## R.sup.4 represents alkyl or unsubstituted or substituted aralkyl, R.sup.5 represents hydrogen or alkyl andZ represents oxygen or sulphur.Type: GrantFiled: October 6, 1992Date of Patent: June 21, 1994Assignee: Bayer AktiengesellschaftInventors: Ulrich Heinemann, Gerd Kleefeld, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5294596Abstract: 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: GrantFiled: July 21, 1993Date of Patent: March 15, 1994Assignee: Bayer AktiengesellschaftInventors: Wilhelm Haas, Kurt Findeisen, Karl-Heinz Linker, Klaus Lurssen, Hans-Joachim Santel, Robert R. Schmidt
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Patent number: 5292737Abstract: N,N'-Bis(sulfonamido)-2-amino-4-iminonaphthalen-1-ones and N,N'-Bis(amido)-2-amino-4-iminonaphthalen-1-ones are disclosed. Methods of inhibiting protein kinase C activity which comprises contacting protein kinase C with an effective amount of an N,N'-Bis(sulfonamido)-2-amino-4-iminonaphthalen-1-one or an N,N'-Bis(amido)-2-amino-4-iminonaphthalen-1-one are disclosed. Methods of treating an animal that is suspected of suffering from inflammatory, cardiovascular and/or neoplastic diseases which comprises administering an effective amount of an N,N'-Bis(sulfonamido)-2-amino-4-iminonaphthalen-1-one or an N,N'-Bis(amido)-2-amino-4-iminonaphthalen-1-one are disclosed.Type: GrantFiled: October 23, 1992Date of Patent: March 8, 1994Assignee: Sphinx Pharmaceuticals CorporationInventor: Jean M. Defauw
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Patent number: 5286881Abstract: A benzodifuranone compounds of the formula, ##STR1## wherein R.sup.1 and R.sup.2 are each independently a naphthyl group or an unsubstituted or substituted phenyl group, which is useful for dyeing or printing hydrophobic fiber materials, is prepared in high purity and high yield by allowing benzofuran compounds of the formula, ##STR2## wherein R.sup.1 is as defined above, to react with acetonitrile compounds of the formula, ##STR3## wherein R.sup.2 is as defined above, and then carrying out an oxidation reaction to give the benzodifuranone compound.Type: GrantFiled: September 30, 1992Date of Patent: February 15, 1994Assignee: Sumitomo Chemical Company LimitedInventors: Junichi Sekihachi, Jun Yamamoto, Yutaka Kayane
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Patent number: 5283363Abstract: The invention relates to a new process for the preparation of (hetero)arylalk(en/in)ylamines of the formula (I) ##STR1## in which A represents ethane-1,2-diyl (ethylene, dimethylene, --CH.sub.2 --CH.sub.2 --) or represents ethene-1,2-diyl (ethenylene, vinylene, --CH.dbd.CH--) or represents ethine-1,2-diyl (ethinylene, --C.ident.C--),characterized in that(a) in the event that, in formula (I), A represents ethine-1,2-diyl, halogeno(hetero)aryl compounds of the general formula (II)Ar--X (II)are reacted with aminoalkinyl compounds of the general formula (III) ##STR2## and, if appropriate, (b) in the event that, in formula (I), A represents ethane-1,2-diyl or ethene-1,2-diyl, the new (hetero)aralkinylamines which are obtained by the process step described under (a), of the general formula (Ia), ##STR3## are reacted with a hydrogenating agent, if appropriate in the presence of a catalyst and if appropriate in the presence of a diluent, the definitions applying to Ar, R.sup.1, R.sup.Type: GrantFiled: January 16, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Dietmar Kuhnt, Thomas Himmler, Heinz Ziemann
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Patent number: 5281614Abstract: Novel substituted triazolinone, triazolinethione, and triazolinimine compounds of the formula I are useful as angiotensin II antagonists.Type: GrantFiled: November 2, 1992Date of Patent: January 25, 1994Assignee: Merck & Co., Inc.Inventors: Wallace T. Ashton, Prasun K. Chakravarty, Linda L. Chang, William J. Greenlee, Dooseop Kim, Nathan B. Mantlo, Arthur A. Patchett
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Patent number: 5276037Abstract: 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: GrantFiled: April 14, 1993Date of Patent: January 4, 1994Assignees: Imperial Chemical Industries PLC, ICI PharmaInventors: Robert I. Dowell, Philip N. Edwards, Keith Oldham
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Patent number: 5243054Type: GrantFiled: June 25, 1992Date of Patent: September 7, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Takehiko Naka, Yoshiyuki Inada
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Patent number: 5223616Abstract: 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: GrantFiled: November 4, 1991Date of Patent: June 29, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Jun Yamamoto, Junichi Sekihachi, Yosuke Yamamoto, Kazuhiro Machiguchi, Yutaka Kayane
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Patent number: 5208248Abstract: A class of indazole-substituted five-membered heteroaromatic compounds are specific agonists of 5-HT.sub.1 -like receptors and are therefore useful in the treatment of clinical conditions, in particular migraine and associated disorders, for which a selective agonist of these receptors is indicated.Type: GrantFiled: July 16, 1991Date of Patent: May 4, 1993Assignee: Merck Sharpe & Dohme, Ltd.Inventors: Raymond Baker, Mark S. Chambers, Leslie J. Street
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Patent number: 5194167Abstract: Quaternary ammonium salts of mercaptothiadiazoles and related heterocyclic derivatives have been found to be effective antioxidant and antiwear additives for lubricants and fuels.Type: GrantFiled: May 8, 1991Date of Patent: March 16, 1993Assignee: Mobil Oil CorporationInventors: Shih-Ying Hsu, Andrew G. Horodysky
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Patent number: 5189175Abstract: Fungicidal thiadiazole-substituted acrylic acid esters of the formula ##STR1## in which R.sup.1 represents hydrogen, unsubstituted or substituted alkyl or alkenyl, or in each case unsubstituted or substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents alkyl,R.sup.3 represents dialkylamino or a radical --Z--R.sup.4,Y represents oxygen, sulphur or a radical ##STR2## R.sup.4 represents alkyl or unsubstituted or substituted aralkyl, R.sup.5 represents hydrogen or alkyl andZ represents oxygen or sulphur.Type: GrantFiled: May 2, 1991Date of Patent: February 23, 1993Assignee: Bayer AktiengesellschaftInventors: Ulrich Heinemann, Gerd Kleefeld, Stefan Dutzmann, Gerd Hanssler
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Patent number: 5186850Abstract: The incorporation of the heterocyclic dimercaptothiadiazole functionality into the alkenylsuccinimide dispersant structures via the Mannich alkylaminomethylkation procedure provides a class of ashless non-phosphorus dispersants with multifunctional antiwear, antioxidant and corrosion inhibitor properties in lubricant compositions.Type: GrantFiled: July 9, 1992Date of Patent: February 16, 1993Assignee: Mobil Oil CorporationInventors: Abraham O. M. Okorodudu, Angeline B. Cardis, Ross A. Kremer
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Patent number: 5155122Abstract: The present invention is novel compounds which are 3,5-di-tertiary-butyl-4-hydroxyphenyl substituted 1,2,4- and 1,3,4-thiadazoles and oxadiazoles, and 1,2,4-triazoles, and pharmaceutically acceptable additions and 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.Type: GrantFiled: August 23, 1991Date of Patent: October 13, 1992Assignee: Warner-Lambert CompanyInventors: David T. Connor, Daniel L. Flynn, Catherine R. Kostlan, Michael D. Mullican, Gary P. Shrum, Paul C. Unangst, Michael W. Wilson
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Patent number: 5128267Abstract: Naphthotriazolium salts which are chromogenic indicators for reducing substrate, such as NADH or NADPH.Type: GrantFiled: February 19, 1991Date of Patent: July 7, 1992Assignee: Miles Inc.Inventors: Jurgen Kocher, Meinhard Rolf, Klaus Wehling
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Patent number: 5124460Abstract: A process for preparing a substantially pure enantiomer of a compound formula (I) ##STR1## wherein X is O or S; andR.sup.2 represents hydrogen, --CF.sub.3, --OR.sup.7, --SR.sup.7, --NR.sup.7 R.sup.8, --CN, --COOR.sup.7, --CONR.sup.7 R.sup.8, or a saturated or unsaturated, substituted or unsubstituted hydrocarbon group, wherein R.sup.7 and R.sup.8 are independently selected from hydrogen and C.sub.1-2 alkyl provided that --NR.sup.7 R.sup.8 is other than NH.sub.2 ;which process comprises cyclization of a compound of formula (10) or salt thereof: ##STR2## wherein X and R.sup.2 are as defined in formula (I); and R.sup.4 is a labile leaving group and optionally epimerizing the endo-diastereomer so prepared to produce the corresponding exo-diastereomer.Type: GrantFiled: May 6, 1991Date of Patent: June 23, 1992Assignee: Merck Sharp & Dohme Ltd.Inventor: Guy R. Humphrey
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Patent number: 5114958Abstract: 1,2,4-Oxadiazole and 1,2,4-thiadiazole derivatives of the fenamic acids, in which the fenamate residue is present at the 3-position of the 1,2,4-oxadiazole or 1,2,4-thiadiazole, pharmaceutically acceptable acid addition or base salts and methods of preparation for such compounds as well as pharmaceutical compositions alone or in combination with a second active ingredient are described. The compounds are active as inhibitors of cyclooxygenase and/or 5-lipoxygenase thereby providing methods of treatment for antiinflammatory diseases.Type: GrantFiled: May 9, 1991Date of Patent: May 19, 1992Assignee: Warner-Lambert CompanyInventors: Diane H. Boschelli, David T. Connor
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Patent number: 5103007Abstract: Lipid derivatives represented by the formula: ##STR1## wherein R.sup.1 stands for an optionally substituted higher alkyl group, R.sup.2 stands for an optionally substituted lower alkyl group or an optionally substituted nitrogen-containing heterocyclic group, R.sup.3 stands for a tertiary amino group or a quaternary ammonium group, J stands for oxygen atom or S(O)t (where t deontes 0, 1 or 2), m and n respectively denotes 1 or 2, p denotes 0, 1 or 2, q and r respectively denote an integer of 2 to 5.and salts thereof have antitumor activities including differentiation-inducing activity and are useful as antitumor agents.Type: GrantFiled: October 27, 1989Date of Patent: April 7, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Keizo Inoue
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Patent number: 5101034Abstract: 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: GrantFiled: March 7, 1991Date of Patent: March 31, 1992Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Hans-Joachim Diehr
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Patent number: 5090991Abstract: Herbicidal N-isopropylheteroaryloxyacetanilides of the formula ##STR1## in which A stands for nitrogen or the group C-R.sup.3 whereR.sup.3 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl or alkylsulphonyl,B stands for nitrogen or the group C-R.sup.4 l whereR.sup.4 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenolakylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, or for the group -CY.sub.2 -Z-R.sup.5 whereR.sup.5 stands for alkyl, which is optionally substituted by halogen, alkoxy or alkylthio, or for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio,Y stands for hydrogen or halogen,Z stands for oxygen, sulphur, SO or SO.sub.2,R.sup.Type: GrantFiled: August 20, 1990Date of Patent: February 25, 1992Assignee: Bayer AkatiengesellschaftInventors: Heinz Forster, Roland Andree, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 5081245Abstract: A compound represented by the formula: ##STR1## wherein R represents a hydrogen atom or a lower alkyl group;R.sup.1 represents a higher alkyl group which may be substituted;R.sup.2 represents a hydrogen atom or a lower alkyl group, a lower alkanoyl group or a nitrogen-containing 5- to 7-membered heterocyclic group each of which may be substituted; X represents a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --wherein p represents an integer of 1 to 5, a divalent group represented by the formula:--O(CH.sub.2).sub.q --wherein q represents an integer of 3 to 8, or a divalent group represented by the formula:--(OCH.sub.2 CH.sub.2).sub.p --J--(CH.sub.2).sub.q --wherein J represents an oxygen atom or a group represented by the formula: --S(O).sub.Type: GrantFiled: August 18, 1989Date of Patent: January 14, 1992Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroaki Nomura, Hiroshi Akimoto, Eiko Imamiya, Keizo Inoue
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Patent number: 5047554Abstract: 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: GrantFiled: January 31, 1990Date of Patent: September 10, 1991Assignee: Pfizer Inc.Inventors: Frederick J. Ehrgott, Carl J. Goddard, Gary R. Schulte
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Patent number: 5036085Abstract: Fungicidal thiadiazole-substituted acrylic acid esters of the formula ##STR1## in which R.sup.1 represents hydrogen, unsubstituted or substituted alkyl or alkenyl, or in each case unsubstituted or substituted aralkyl, aralkenyl, aryl or heteroaryl,R.sup.2 represents alkyl,R.sup.3 represents dialkyl amino or a radical --Z--R.sup.4,Y represents oxygen, sulphur or a radical ##STR2## R.sup.4 represents alkyl or unsubstituted or substituted aralkyl, R.sup.5 represents hydrogen or alkyl andZ represents oxygen or sulphur.Type: GrantFiled: March 19, 1990Date of Patent: July 30, 1991Assignee: Bayer AktiengesellschaftInventors: Ulrich Heinemann, Gerd Kleefeld, Stefan Dutzmann, Gerd Hanssler
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Patent number: 4985450Abstract: There are described compounds of the formula ##STR1## where n is 0, 1 or 2; x and y are independently hydrogen, loweralkyl, loweralkoxy, arylloweralkyl, aryloxy, halogen, --CF.sub.3, --NO.sub.2, --OH, --OCOR.sub.1, ##STR2## where R.sub.1 is loweralkyl, arylloweralkyl, aryl or loweralkoxy, R.sub.2 is hydrogen, loweralkyl or loweralkylcarbonyl, R.sub.3 is hydrogen or loweralkyl, or the group --NR.sub.2 R.sub.3 whole is ##STR3## m is 0, 1 or 2, and R.sub.4 is hydrogen, loweralkyl or aryl; and Z is (R.sub.5, R.sub.6), ##STR4## where R.sub.5 and R.sub.6 are each independently hydrogen or loweralkyl, R.sub.7 loweralkyl, R.sub.8 is hydrogen, loweralkyl or aryl, R.sub.9 and R.sub.10 are each independently loweralkyl or the group --NR.sub.9 R.sub.10 as a whole is ##STR5## R.sub.12 being hydrogen, loweralkyl or aryl, and R.sub.11 is hydrogen, loweralkyl or aryl; which are useful for the treatment of glaucoma.Type: GrantFiled: August 14, 1989Date of Patent: January 15, 1991Inventors: John J. Tegeler, Kirk D. Shoger
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Patent number: 4968342Abstract: Herbicidal N-isopropylheteroaryloxyacetanilides of the formula ##STR1## in which A stands for nitrogen or the group C--R.sup.3 whereR.sup.3 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl or alkylsulphonyl,B stands for nitrogen or the group C--R.sup.4 whereR.sup.4 stands for halogen, cyano, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, or for the group --CY.sub.2 --Z--R.sup.5 whereR.sup.5 stands for alkyl, which is optionally substituted by halogen, alkoxy or alkylthio, or for phenyl which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio,Y stands for hydrogen or halogen,Z stands for oxygen, sulphur, SO or SO.sub.2,R.sup.Type: GrantFiled: June 15, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Roland Andree, Hans-Joachim Santel, Robert R. Schmidt, Harry Strang
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Patent number: 4954518Abstract: 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: GrantFiled: October 7, 1988Date of Patent: September 4, 1990Assignee: Toyama Chemical Company, Ltd.Inventors: Shuntaro Takano, Chosaku Yoshida, Takihiro Inaba, Keiichi Tanaka, Ryuko Takeno, Hideyoshi Nagaki, Tomoya Shimotori, Shinji Makino
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Patent number: 4952580Abstract: 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: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen
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Patent number: 4952599Abstract: 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: GrantFiled: July 20, 1988Date of Patent: August 28, 1990Assignee: Ciba-Geigy CorporationInventors: Josef Ehrenfreund, Manfred Boger, Jozef Drabek
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Patent number: 4950764Abstract: 2-Aryl-4-isoxazolin-3-one derivatives having the following general formula (I): ##STR1## wherein R.sup.1 represents an alkyl group or an aryl group, R.sup.2, R.sup.3, and R.sup.4 each represents a hydrogen atom, a trifluoromethyl group, a carbamoyl group, a sulfamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a sulfonyl group, a halogen atom, a cyano group, a nitro group, an alkoxy group, an aryloxy group, an acyl group, a carboxy group, or a sulfo group, with at least one of R.sup.2, R.sup.3, and R.sup.4 being selected from among a nitro group, a cyano group, a sulfamoyl group, a carbamoyl group, and a sulfonyl group, and X represents a monovalent group of one of a mercaptoazole, a mercaptoazaindene, a tetrazaindene, a mercaptopyrimidine a benzotriazole, an indazole, and a benzimiazole, are disclosed.Type: GrantFiled: May 2, 1988Date of Patent: August 21, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Koki Nakamura, Shigeru Makamura
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Patent number: 4943584Abstract: 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: GrantFiled: April 20, 1988Date of Patent: July 24, 1990Assignee: BASF AktiengesellschaftInventors: Hans Theobald, Christoph Kuenast, Peter Hofmeister, Hans-Juergen Neubauer, Thomas Kuekenhoehner, Wolfgang Krieg, Joachim Leyendecker, Uwe Kardorff
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Patent number: 4920231Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.Type: GrantFiled: March 30, 1989Date of Patent: April 24, 1990Assignee: Roussel UclafInventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
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Patent number: 4906393Abstract: Mixed phenol/dimercaptothiadiazole-derived hydroxythioether borates have been found to be effective antiwear/antioxidant multifunctional additives for lubricants.Type: GrantFiled: December 30, 1988Date of Patent: March 6, 1990Assignee: Mobil Oil CorporationInventors: Liehpao O. Farng, Andrew G. Horodysky, William F. Olszewski
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Patent number: 4891432Abstract: Novel phenoxy derivatives are provided which can be represented by the general formula: ##STR1## wherein the various substituents are as defined, and include compounds such as benzyl 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoate.The invention also encompasses pharmaceutical compositions containing the derivatives and their use in treating tumors.Type: GrantFiled: July 16, 1987Date of Patent: January 2, 1990Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Noriki Ito, Yoshinobu Nagano, Akihiro Tanaka, Yoso Numasaki, Koichiro Takahashi
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Patent number: 4888348Abstract: 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: GrantFiled: August 28, 1987Date of Patent: December 19, 1989Assignee: Ciba-Geigy CorporationInventors: Josef Ehrenfreund, Manfred Boger, Odd Kristiansen, Jozef Drabek, Haukur Kristinsson
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Patent number: 4873239Abstract: There are described compounds of the formula ##STR1## where n is 0, 1 or 2; X and Y are independently hydrogen, loweralkyl, loweralkoxy, arylloweralkyl, aryloxy, halogen, --CF.sub.3, --NO.sub.2, --OH, --OCOR.sub.1, ##STR2## where R.sub.1 is loweralkyl, arylloweralkyl, aryl or loweralkoxy, R.sub.2 is hydrogen, loweralkyl or loweralkylcarbonyl, R.sub.3 is hydrogen or loweralkyl, or the group --NR.sub.2 R.sub.3 as a whole is ##STR3## m is 0, 1 or 2, and R.sub.4 is hydrogen, loweralkyl or aryl; and Z is (R.sub.5,R.sub.6), ##STR4## where R.sub.5 and R.sub.6 are each independently hydrogen or loweralkyl, R.sub.7 is loweralkyl, R.sub.8 is hydrogen, loweralkyl or aryl, R.sub.9 and R.sub.10 are each independently loweralkyl or the group --NR.sub.9 R.sub.10 as a whole is ##STR5## R.sub.12 being hydrogen, loweralkyl or aryl, and R.sub.11 is hydrogen, loweralkyl or aryl; which are useful for the treatment of glaucoma.Type: GrantFiled: May 3, 1988Date of Patent: October 10, 1989Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventors: John J. Tegeler, Kirk D. Shoger
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Patent number: 4871719Abstract: Novel 13-spiro-2'-[tetrahydrofuran]-milbemycins of the formula I ##STR1## in which X represents one of the groups --CH(OR.sub.1)--, --C(.dbd.O)-- or --C(.dbd.N--OH)--;R.sub.1 represents hydrogen or a OH-protecting group;R.sub.2 represents methyl, ethyl, isopropyl or sec.-butyl or the group --C(CH.sub.3).dbd.CH--A in which A represents methyl, ethyl or isopropyl; andR.sub.3 represents hydrogen; C.sub.1 -C.sub.10 -alkyl; C.sub.1 -C.sub.10 -alkyl substituted by at least one substituent selected from the group consisting of halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.2 -C.sub.6 -alkoxyalkoxy C.sub.3 -C.sub.9 -alkoxyalkoxyalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.3 -alkyl-substituted C.sub.3 -C.sub.7 -cycloalkyl, hydroxy, benzyloxy, C.sub.1 -C.sub.6 -acyl and C.sub.1 -C.sub.6 -acyloxy, it being possible for each of the above-mentioned radicals representing or containing an alkoxy group to be terminally substituted at a terminal alkoxy group by hydroxy, halogen, C.sub.1 -C.sub.Type: GrantFiled: March 16, 1988Date of Patent: October 3, 1989Assignee: Ciba-Geigy CorporationInventor: Peter Maienfisch
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Patent number: 4863945Abstract: 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: GrantFiled: December 10, 1987Date of Patent: September 5, 1989Assignee: Boehringer Mannheim GmbHInventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
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Patent number: 4855310Abstract: Novel heterocyclic compounds shown by the general formula ##STR1## or the pharmaceutically acceptable salts thereof useful as medicament in particular as antagonist of slow reacting substance of anaphylaxis (SRS-A).Type: GrantFiled: March 25, 1988Date of Patent: August 8, 1989Assignee: Yamanouchi Pharmaceutical Co., Ltd.Inventors: Kiyoshi Murase, Toshiyasu Mase, Hiromu Hara, Kenichi Tomioka
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Patent number: 4851406Abstract: 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: GrantFiled: September 4, 1986Date of Patent: July 25, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
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Patent number: 4833252Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings:R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.Type: GrantFiled: September 28, 1988Date of Patent: May 23, 1989Assignee: Ciba-Geigy CorporationInventors: Werner Topfl, Georg Pissiotas
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Patent number: 4831032Abstract: 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: GrantFiled: July 3, 1986Date of Patent: May 16, 1989Assignee: Boehringer Mannheim GmbHInventors: Wolfgang von der Saal, Alfred Mertens, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein