Nitrogen Attached Directly To The Oxadiazole Ring By Nonionic Bonding Patents (Class 548/133)
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Patent number: 5256632Abstract: 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: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Bayer AktiengesellschaftInventors: Hilmar Wolf, Rolf Kirsten, Hans-Joachim Santel, Klaus Lurssen, Robert R. Schmidt
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Patent number: 5256680Abstract: 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: June 29, 1992Date of Patent: October 26, 1993Assignee: 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: 5242890Abstract: The present invention relates to 1,2,4-oxadiazole derivative of the formula (I) ##STR1## wherein X represents a chlorine or fluorine atom or methyl group,Y represents a chlorine or fluorine atom,n is an integer of 1 or 3.The compounds of the invention have a extremely high selectively between paddy rice or crop plants and weeds, and a strong activity on various weeds. Moreover, the compounds have a very low phytotoxicity to paddy rice and crop plants.Type: GrantFiled: February 3, 1992Date of Patent: September 7, 1993Assignee: Korea Research Institute of Chemical TechnologyInventors: Kwang Y. Cho, In H. Jeong
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Patent number: 5242927Abstract: A class of novel oxadiazoles, substituted on one of the ring carbon atoms with a non-aromatic azacyclic or azabicyclic ring and on the other ring carbon atom with a substituent which is convertible in vivo to an amino group, are potent muscarinic agonists, and exhibit improved CNS penetrability and duration of action compared with the corresponding amino compounds. The compounds are therefore useful in the treatment of neurological and mental illnesses.Type: GrantFiled: July 18, 1988Date of Patent: September 7, 1993Assignee: Merck Sharp & Dohme LimitedInventors: Raymond Baker, John Saunders, Angus M. MaCleod, Graham A. Showell
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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: 5221676Abstract: 7-Substituted quinolones and naphthyridones are described as antibacterial agents as well as a process for their manufacture, compositions therefor, wherein the 7-substituent is a pyrrolidine ring substituted at the 3-position by a substituted aromatic hydrocarbon or a heteroaromatic group.Type: GrantFiled: February 6, 1992Date of Patent: June 22, 1993Assignee: Warner-Lambert CompanyInventors: Edgardo Laborde, Mel Schroeder
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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: 5207816Abstract: 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: GrantFiled: June 6, 1991Date of Patent: May 4, 1993Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Dieter Jahn, Michael Keil, Hans Theobald, Wolfgang Spiegler, Bruno Wuerzer
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Patent number: 5185353Abstract: A method for killing or controlling nematode pests which comprises applying to the locus of the pests or to a plant susceptible to attack by the pest an effective amount of a compound of formula (I): ##STR1## wherein R.sup.1 is an optionally substituted aryl or optionally substituted heterocyclic group and novel compounds of formula (I) where R.sup.1 is not phenyl.Type: GrantFiled: November 8, 1990Date of Patent: February 9, 1993Assignee: Imperial Chemical Industries PLCInventors: Michael D. Turnbull, Robert W. Parsons, Andrew D. S. Watkins
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Patent number: 5180731Abstract: A compound of the formula: ##STR1## wherein A is the group of the formula:Ar.sup.1 --D--Ar.sup.2 --wherein Ar.sup.1 is a phenyl or thienyl group which may be optionally substituted with at least one of the same or different halogen atom; Ar.sup.2 is a phenylene or thienylene group which may be optionally substituted with at least one of the same or different halogen atom; D is a divalent radical selected from the group consisting of >C.dbd.N--OR .sup.4 [wherein R.sup.4 is a hydrogen atom or lower alkyl group], >C.dbd.O, ##STR2## >CHOH, >NH radical, or single bond, ##STR3## wherein R.sup.5 is a lower alkoxy or phenyl group which may be optionally substituted with at least one of the same or different halogen atom; E is a methine group or a nitrogen atom; F is a vinylene group or an oxygen atom, ##STR4## wherein R.sup.6 is a lower alkoxy group; R.sup.7 is a lower alkyl group; R.sup.Type: GrantFiled: July 18, 1991Date of Patent: January 19, 1993Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Yukinori Ozato, Nobuhiko Tamura, Hiroaki Masumori, Michihiro Yamamoto, Atsuyuki Kojima, Fumio Nishikaku, Yoshihiko Kimura
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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: 5112841Abstract: Described herein are imidazole derivatives having a specific structure and satisfactory as antiepileptics from the standpoint of the strength of action, prolonged action and side effects as well as their preparation processes.Type: GrantFiled: February 28, 1991Date of Patent: May 12, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Akira Matsubara, Kazuya Sakai, Hideki Tanada, Akira Mizuchi, Kazutoshi Horikomi, Takuma Ohtsu
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Patent number: 5068365Abstract: Disclosed is novel hexahydrophthalic anilide derivatives and herbicide compositions comprising the derivatives. The hexahydrophthalic anilide derivatives of this invention are represented by the formula [I], [II] or [III]. ##STR1## (wherein R.sup.1 represents non-substituted or substituted phenyl, R.sup.2 represents hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkenyl) ##STR2## (wherein R.sup.4 and R.sup.5, the same or different, represent C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, provided R.sup.4 and R.sup.5 are not C.sub.1 -C.sub.4 alkyl simultaneously) ##STR3## (wherein X.sup.1 and X.sup.2, the same or different, represent halogen, Y represents oxygen or sulfur, R.sup.6 represents C.sub.1 -C.sub.6 straight or cyclic alkyl which may be substituted with oxygen, R.sup.7 represents hydrogen or methyl, R.sup.8 represents cyano, C.sub.1 -C.sub.3 alkyl, C.sub.2 or C.sub.3 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.Type: GrantFiled: December 30, 1988Date of Patent: November 26, 1991Assignees: Tosoh Corporation, Agro-Kanesho Co., Ltd.Inventors: Takumi Tokunaga, Hiroyuki Watanabe, Kenji Tsuzuki, Sinzo Someya, Seigo Koura, Mikio Ito
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Patent number: 5066666Abstract: compound of the formula: ##STR1## wherein A is the group of the formula:Ar.sup.1 --D--Ar.sup.2 --wherein Ar.sup.1 is a phenyl or thienyl group which may be optionally substituted with at least one of the same or different halogen atom; Ar.sup.2 is a phenylene or thienylene group which may be optionally substituted with at least one of the same or different halogen atom; D is a divalent radical selected from the group consisting of >.dbd.N.dbd.OR.sup.4 [wherein R.sup.4 is a hydrogen atom or lower alkyl group], >C.dbd.O, ##STR2## >CHOH, >NH radical, or single bond, wherein R.sup.5 is a lower alkoxy or a phenyl group which may be optionally substituted with at least one of the same or different halogen atom; E is a methine group or a nitrogen atom; F is a vinylene group or an oxygen atom, ##STR3## wherein R.sup.6 is a lower alkoxy group; R.sup.7 is a lower alkyl group; R.sup.Type: GrantFiled: January 26, 1990Date of Patent: November 19, 1991Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Yukinori Ozato, Nobuhiko Tamura, Hiroaki Masumori, Michihiro Yamamoto, Atsuyuki Kojima, Fumio Nishikaku, Yoshihiko Kimura
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Patent number: 5051421Abstract: Benzo[b]thiophene derivatives of formula ##STR1## their tautomers and salts, in which the index n is 0, 1 or 2, alk is lower alkylene, Ar is phenyl, naphthyl or a monocyclic, five- or six-membered heteroaryl radical, wherein the aromatic radical is unsubstituted or is mono- or poly-substituted by lower alkyl, halo-lower alkyl, halogen and/or by nitro, and the ring A is unsubstituted or is mono- or poly-substituted by lower alkyl, lower alkoxy, lower alkylthio, lower alkanesulfinyl, lower alkanesulfonyl, halo-lower alkyl, halogen and/or by nitro, can be used, for example, as active ingredients in medicaments.Type: GrantFiled: January 18, 1990Date of Patent: September 24, 1991Assignee: Ciba-Geigy CorporationInventor: Pier G. Ferrini
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Patent number: 5041456Abstract: The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted circle represents one or two double bonds in any position in the 5-membered ring;X, Y and Z independently represent oxygen, sulphur, nitrogen or carbon, provided that at least one of X, Y and Z represents oxygen, sulphur or nitrogen;A represents a group of formula II: ##STR2## in which: R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, hydroxy(C.sub.1-6)alkyl, halogen, amino, cyano, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl;R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarobnyl;V represents nitrogen, ##STR3## W represents oxygen, sulphur or ##STR4## in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.Type: GrantFiled: July 13, 1990Date of Patent: August 20, 1991Assignee: Merck Sharp & Dohme Ltd.Inventors: Raymond Baker, John Saunders, Christopher Swain
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Patent number: 4988706Abstract: 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: GrantFiled: April 13, 1989Date of Patent: January 29, 1991Assignee: Beecham Group P.L.C.Inventors: Michael S. Hadley, Barry S. Orlek, Paul A. Wyman, Harry J. Wadsworth
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Patent number: 4914112Abstract: A compound of the formula: ##STR1## wherein A is the group of the formula:Ar.sup.1 --D--Ar.sup.2 --wherein Ar.sup.1 is a phenyl or thienyl group which may be optionally substituted with at least one of the same or different halogen atom; Ar.sup.2 is a phenylene or thienylene group which may be optionally substituted with at least one of the same or different halogen atom; D is a divalent radical selected from the group consisting of >C.dbd.N--OR.sup.4 [wherein R.sup.4 is a hydrogen atom or lower alkyl group], >C.dbd.O, ##STR2## >CHOH, >NH radical, or single bond, ##STR3## wherein R.sup.5 is a lower alkoxy or a phenyl group which may be optionally substituted with at least one of the same or different halogen atom; E is a methine group or a nitrogen atom; F is a vinylene group or an oxygen atom, ##STR4## wherein R.sup.6 is a lower alkoxy group; R.sup.7 is a lower alkyl group; R.sup.Type: GrantFiled: May 28, 1987Date of Patent: April 3, 1990Assignee: Sumitomo Pharmaceuticals Company, LimitedInventors: Yukinori Ozato, Nobuhiko Tamura, Hiroaki Masumori, Michihiro Yamamoto, Atsuyuki Kojima, Fumio Nishikaku, Yoshihiko Kimura
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Patent number: 4882342Abstract: The present invention concerns new 5-alkylbenzimidazoles of the formula: ##STR1## wherein R.sub.1 is a phenyl ring of the formula: ##STR2## or R.sub.1 is naphthyl, heterocycle or a bicyclic heterocycle and R.sub.1 -R.sub.7 are described in claim 1.These compounds are useful for prophylaxis or treatment of heart and circulatory disease especially to increase contractility of the heart, lower blood pressure and/or influence the thrombocyte function and improve the microcirculation.Type: GrantFiled: October 6, 1987Date of Patent: November 21, 1989Assignee: Boehringer Mannheim GmbHInventors: Wolfgang von der Saal, Jens-Peter Holck, Alfred Mertens, Bernd Muller-Beckmann, Lothar Kling
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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: 4835280Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.Type: GrantFiled: July 14, 1987Date of Patent: May 30, 1989Assignee: Boehringer Mannheim GmbHInventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
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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
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Patent number: 4810282Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.Type: GrantFiled: June 10, 1987Date of Patent: March 7, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer
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Patent number: 4801718Abstract: N-Aryl benzamides wherein the aryl group is a nitrogen containing heterocycle are useful as selective herbicidal agents. Compositions containing the novel benzamides and a herbicidal method of selective weed control are disclosed.Type: GrantFiled: December 5, 1985Date of Patent: January 31, 1989Assignee: Eli Lilly and CompanyInventor: Kenneth W. Burow, Jr.
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Patent number: 4797492Abstract: A novel compound useful as an intermediate for synthesizing pesticides and medicines of the formula: ##STR1## in which: R is alkyl having plural florines; R.sup.1 is hydrogen, alkyl, halogen or optionally substituted phenyl; and R.sup.2 is hydrogen or alkyl, or a salt thereof.Type: GrantFiled: October 22, 1986Date of Patent: January 10, 1989Assignee: Shionogi & Co., Ltd.Inventors: Shinzaburo Sumimoto, Ichiro Ishizuka, Hiroyuki Kai, Shiro Ueda, Akira Takase
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Patent number: 4795755Abstract: This invention relates to heterocyclic derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen-substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 -E-W- in which W is 2-6 alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O,S,SO,SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: January 3, 1989Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4772622Abstract: Novel diamino oxadiazoles, wherein one of the amine functions is connected to a basicly-substituted heterocyclic group through a linear or cyclic connecting group, which are useful for the suppression of gastric acid secretions in mammals. Compositions employing these compounds and processes for the preparation of such compounds from known N-cyano-S-methylisothiourea precursors by treatment with hydroxylamine and for alkylation of amine groups are also disclosed.Type: GrantFiled: June 16, 1986Date of Patent: September 20, 1988Assignee: Merck & Co., Inc.Inventors: Susan F. Britcher, William C. Lumma, Jr.
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Patent number: 4762932Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.Type: GrantFiled: June 2, 1986Date of Patent: August 9, 1988Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
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Patent number: 4742060Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.Type: GrantFiled: January 21, 1986Date of Patent: May 3, 1988Assignee: Nihon Tokushu Noyaku Seizo K. K.Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
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Patent number: 4740231Abstract: 1-Aryl-5-alkoximinoalkylamino-pyrazoles of the formula ##STR1## in which R represents cyano or nitro, or represents an optionally substituted heterocyclic radical,R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen or alkyl, or represents optionally substituted aryl,R.sup.3 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl or aryl andAr represents optionally substituted phenyl or pyridyl,are active as herbicides and plant growth regulants. Compounds of the formula ##STR2## in which R" has the same definition as R other than cyano, are also active and useful as intermediates as well.Type: GrantFiled: May 22, 1986Date of Patent: April 26, 1988Assignee: Bayer AktiengesellschaftInventors: Reinhold Gehring, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
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Patent number: 4714707Abstract: Aryl substituted diazaheterocyclic amines and their use in the treatment of gastrointestinal motility dysfunctions.Type: GrantFiled: January 13, 1984Date of Patent: December 22, 1987Assignee: Rorer Pharmaceutical CorporationInventors: Donald E. Kuhla, William L. Studt, Henry F. Campbell, John Yelnosky
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Patent number: 4696933Abstract: The invention relates to amide derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 is a hydrogen or 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl, the aryl, aralkyl and aroyl radical being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene, or a 1-8C alkylene into which is optionally inserted one or two groups; D is O or S; and R.sup.2 and R.sup.3 are hydrogen or a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.Type: GrantFiled: February 12, 1985Date of Patent: September 29, 1987Assignees: ICI Americas Inc., Imperial Chemical Industries PLCInventors: Tobias O. Yellin, David J. Gilman
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Patent number: 4695311Abstract: This invention relates to ortho-(isoxazolyl, isothiazolyl, pyrazolyl, thiadiazolyl, oxadiazolyl, and triazolyl)benzenesulfonamides and their use as herbicides.Type: GrantFiled: May 9, 1986Date of Patent: September 22, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Morris P. Rorer
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Patent number: 4695567Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.Type: GrantFiled: January 17, 1986Date of Patent: September 22, 1987Assignee: Boehringer Mannheim GmbHInventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
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Patent number: 4692531Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.Type: GrantFiled: September 25, 1986Date of Patent: September 8, 1987Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4689335Abstract: A method for treating gastrointestinal motility dysfunctions using phenylheterocyclic guanidines and novel heterocyclic guanidine compounds.Type: GrantFiled: January 13, 1984Date of Patent: August 25, 1987Assignee: William H. Rorer, Inc.Inventors: Donald E. Kuhla, William L. Studt, Henry F. Campbell, John Yelnosky
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Patent number: 4659836Abstract: Imidazolidinone imines are provided as well as a process for preparing same including corresponding imidazolidinone amines which compounds are useful as herbicides.Type: GrantFiled: August 5, 1986Date of Patent: April 21, 1987Assignee: PPG Industries, Inc.Inventor: James A. Schwindeman
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Patent number: 4645841Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms; tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.Type: GrantFiled: June 24, 1985Date of Patent: February 24, 1987Assignee: Istituto de Angeli, S.p.A.Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero Del Soldato, Antonio Giachetti, Rosamaria Micheletti
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Patent number: 4644006Abstract: Histamine H.sub.2 -receptor antagonists of the formula ##STR1## wherein A, m, Z, n and R.sup.Type: GrantFiled: June 22, 1984Date of Patent: February 17, 1987Assignee: Bristol-Myers CompanyInventors: Aldo A. Algieri, Ronnie R. Crenshaw
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Patent number: 4642312Abstract: Fungicidally active novel N-(3-chloro-1,2,4-oxadiazol-5-yl)-ureas of the formula ##STR1## in which R is alkyl, halogenoalkyl, or optionally substituted cycloalkyl, cycloalkylalkyl or aryl.Type: GrantFiled: November 25, 1985Date of Patent: February 10, 1987Assignee: Bayer AktiengesellschaftInventors: Ulrich Heinemann, Hans-Joachim Knops, Karl Steinbeck, Wilhelm Brandes, Gerd Hanssler, Paul Reinecke
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Patent number: 4634779Abstract: There are described novel dyes of the formulae ##STR1## in which R.sub.1 and R.sub.2 independently of one another are each hydrogen, unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, and R.sub.1 and R.sub.2 together with the nitrogen atom, and optionally with the inclusion of further hetero atoms, can also form a 5- to 7-membered heterocycle, or one of the radicals R.sub.1 or R.sub.2 can be linked with the carbon atom, in the o-position with respect to the amino group, of the ring A to form a fused-on, saturated, unsubstituted or substituted 5- or 6-membered ring,X is .dbd.NR.sub.3, .dbd.NCOR.sub.4, ##STR2## .dbd.NH or .dbd.O, wherein R.sub.3 is alkyl or unsubstituted or substituted phenyl,R.sub.4 is unsubstituted or substituted alkyl, aralkyl, aryl, vinyl, alkoxy, phenoxy or amino, andR.sub.5 is cyano, carbalkoxy, or unsubstituted or substituted carbonamide, andR.sub.Type: GrantFiled: September 30, 1982Date of Patent: January 6, 1987Assignee: Ciba-Geigy CorporationInventor: Peter Mockli
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Patent number: 4618617Abstract: This disclosure describes novel 5-substituted 1,2,4-oxadiazoles useful as pharmaceuticals such as anti-inflammatory and analgesic agents.Type: GrantFiled: February 24, 1983Date of Patent: October 21, 1986Assignee: Sumitomo Chemical Company, LimitedInventor: Michihiro Yamamoto
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Patent number: 4612038Abstract: The invention relates to herbicidally active 3-oxadiazolyl-2-imidazolidinone derivatives, including herbicidal formulation and the use thereof to control the growth of noxious plants, i.e., weeds.Type: GrantFiled: June 24, 1985Date of Patent: September 16, 1986Assignee: PPG Industries, Inc.Inventors: Barry Van Gemert, Jerome M. Lavanish, James A. Schwindeman
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Patent number: 4548944Abstract: Compounds of the tautomeric formula ##STR1## wherein R, R.sub.1 and R.sub.2, which may be identical to or different from each other, are each hydrogen or alkyl of 1 to 4 carbon atoms;R.sub.3 is straight or branched alkyl, optionally interrupted by heteroatoms such as oxygen, sulfur or nitrogen; straight or branched alkenyl; alkynyl; cyano; cycloalkyl or cycloaliphatic alkyl; a bicyclic group; aryl; or a heterocyclic group; orR.sub.2 and R.sub.3, together with each other and the nitrogen atoms to which they are attached, form a heterocyclic group;R.sub.4 is hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; andHet is a substituted or unsubstituted heterocycle containing two or three heteroatoms;tautomers thereof, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as anti-ulcerogenics.Type: GrantFiled: February 10, 1983Date of Patent: October 22, 1985Assignee: Istituto de Angeli S.p.A.Inventors: Giuseppe Bietti, Enzo Cereda, Arturo Donetti, Piero del Soldato, Antonio Giachetti, Rosamaria Micheletti
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Patent number: 4500343Abstract: 1-Heterocyclic-2-pyrrolidinone analogs, and intermediates thereof, as aquatic and terrestrial herbicides and aquatic algicides. The compounds and intermediates can also be used together with one or more herbicides to provide useful terrestrial herbicidal combinations.Type: GrantFiled: September 30, 1982Date of Patent: February 19, 1985Assignee: Eli Lilly and CompanyInventor: Kenneth W. Burow, Jr.
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Patent number: 4496571Abstract: The invention relates to carbonyl derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention where is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.5 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.6 in which R.sup.6 is H or 1-6C alkyl, R.sup.5 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.5 and R.sup.6 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: January 29, 1985Assignees: ICI Americas Inc., Imperial Chemical Industries, PLCInventors: Tobias O. Yellin, David J. Gilman, Philip N. Edwards, Michael S. Large, Derrick F. Jones, Keith Oldham
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Patent number: 4493840Abstract: This invention relates to quanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion.The quanidine derivatives are of the formula:Het.sup.1 --(CH.sub.2).sub.m --Y.sup.1 --(CH.sub.2).sub.n --NR.sup.1 --A--NR.sup.2 --(CH.sub.2).sub.q --Y.sup.2 --(CH.sub.2).sub.p --Het.sup.2.Type: GrantFiled: October 26, 1981Date of Patent: January 15, 1985Assignees: Imperial Chemical Industries PLC, ICI Americas, Inc.Inventors: Tobias O. Yellin, David J. Gilman
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Patent number: 4488895Abstract: Novel N-Diazolylalkyl-haloacetanilides of the formula ##STR1## wherein A is oxygen, sulphur or the grouping <NR,wherein R is hydrogen or alkyl,R.sup.1 is hydrogen, alkyl or alkoxy,R.sup.2 is hydrogen, alkyl, alkoxy or halogen,R.sup.3 is hydrogen, alkyl, alkoxy or halogen,R.sup.4 is hydrogen or alkyl,X is hydrogen, alkyl, halogen, alkoxy, alkylthio, haloalkyl, alkenyl, alkynyl, alkoxycarbonyl, dialkylamino, cyano, phenyl, substituted phenyl, phenoxy, substituted phenoxy, phenylthio or substituted phenylthio, andZ is halogen,and in which the diazolyl radical is bonded via a carbon atom, and acid addition salts and metal salt complexes thereof.Type: GrantFiled: January 28, 1982Date of Patent: December 18, 1984Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Klaus Ditgens, Rudolf Thomas, Ludwig Eue, Robert R. Schmidt
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Patent number: 4460584Abstract: The invention relates to nitrogen heterocycles which are histamine H-2 antagonists and which inhibit gastric acid secretion. According to the invention there is provided a guanidine derivative of the formula I: ##STR1## in which R.sup.1 and R.sup.2, same or different, are hydrogen or 1-10C alkyl, 3-8C cycloalkyl or 4-14C cycloalkylalkyl, each alkyl, cycloalkyl or cycloalkylalkyl optionally carrying one or more F, Cl or Br atoms, provided that one of R.sup.1 and R.sup.2 is halogen substituted, or R.sup.2 is hydrogen and R.sup.1 is R.sup.3 -E-W in which W is 2-6C alkylene optionally substituted by 1 or 2 1-4C alkyls, E is O, S, SO, SO.sub.2 or NR.sup.4 in which R.sup.4 is H or 1-6C alkyl, R.sup.3 is H or 1-6C alkyl optionally substituted by 1 or 2 1-4C alkyls, or R.sup.3 R.sup.4 are joined to form a pyrrolidine, piperidine, morpholine, piperazine or N-methylpiperazine ring, or R.sup.2 is H and R.sup.Type: GrantFiled: March 9, 1982Date of Patent: July 17, 1984Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham