1,2,4-thiadiazoles (including Hydrogenated) Patents (Class 548/128)
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Patent number: 4537903Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.Type: GrantFiled: October 12, 1983Date of Patent: August 27, 1985Assignee: Merck & Co., Inc.Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
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Patent number: 4532250Abstract: Described are compounds of the formula ##STR1## wherein R is heteroaryl and R.sub.1 is hydrogen or loweralkyl, or a pharmaceutically acceptable salt thereof.The compounds exhibit cardiotonic activity.Type: GrantFiled: November 23, 1983Date of Patent: July 30, 1985Assignee: American Hospital Supply CorporationInventors: David M. Stout, Diane M. Yamamoto
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Patent number: 4504304Abstract: Novel compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are H or alkyl and R is an optionally-substituted unsaturated, cycloalkyl, secondary-alkyl, aromatic or heterocyclic group, are useful as plant growth regulators and herbicides. Certain intermediates are also novel.Type: GrantFiled: August 29, 1983Date of Patent: March 12, 1985Assignee: Shell Oil CompanyInventors: Herbert Estreicher, George B. Payne
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Patent number: 4500340Abstract: Urea derivatives of the formula ##STR1## where R, X, Z, Het and n have the meanings given in the description, are used for controlling undesirable plant growth.Type: GrantFiled: November 22, 1982Date of Patent: February 19, 1985Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Hans Theobald, Ulrich Schirmer, Wolfgang Spiegler, Walter Seufert, Bruno Wuerzer
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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: 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: 4468515Abstract: This invention relates to thiadiazolyl compounds useful as intermediates in the preparation of novel cephem compounds of high antimicrobial activity.Type: GrantFiled: November 25, 1981Date of Patent: August 28, 1984Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
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Patent number: 4463005Abstract: The invention relates to bicyclic 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 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 and 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 10, 1982Date of Patent: July 31, 1984Assignee: Imperial Chemical Industries PLCInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4461900Abstract: The compound of formula: ##STR1## where R.sub.1 and R.sub.2 are hydrogen or alkyl;R is ##STR2## R.sub.3 and R.sub.4 are hydrogen, alkyl or alkylene; R.sub.5 and R.sub.6 are hydrogen, alkyl or alkylene;m is 1 to 6 and n is 2 to 6; and,R.sub.7 is hydrogen or alkyl;or a pharmaceutically acceptable salt thereof, are H.sub.2 -receptor antagonists useful in the treatment of peptic ulcer disease.Type: GrantFiled: March 14, 1983Date of Patent: July 24, 1984Assignee: American Home Products CorporationInventor: Dieter H. Klaubert
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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
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Patent number: 4460580Abstract: The invention relates to novel N-alkylated aminoalcohols of the formula ##STR1## in which Ar is a radical of aromatic character which is unsubstituted or substituted by hydroxyl, n has the values nought or 1 and Alk is an alkylene radical having 2 to 5 carbon atoms and the nitrogen atom and the oxygen atom or, if n is nought, the salicylamide radical are separated from one another by at least two carbon atoms in the straight-chain, and their salts. The main action of the novel compounds consists in a stimulation of cardiac .beta.-receptors; the compounds also effect a blockage of adrenergic .alpha.-receptors and a lowering in the blood pressure. They can therefore be used as .beta.-stimulators, especially as agents having a positively inotropic action for the treatment of cardiac insufficiency.Type: GrantFiled: June 24, 1982Date of Patent: July 17, 1984Assignee: Ciba-Geigy CorporationInventors: Franz Ostermayer, Markus Zimmermann
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Patent number: 4456565Abstract: Acyl cyanides of the general formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms; cycloalkyl or substituted cycloalkyl with 3 to 12 carbon atoms; aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can additionally also be fused with a benzene ring, are prepared by reacting the corresponding carboxylic acid anhydride in the liquid phase with anhydrous hydrocyanic acid, at a temperature of between 50.degree. to 250.degree. C.Type: GrantFiled: July 14, 1983Date of Patent: June 26, 1984Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Herbert Schwarz
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Patent number: 4455264Abstract: Acyl cyanides of the formula ##STR1## in which R represents an optionally substituted alkyl group having 1 to 8 carbon atoms, an optionally substituted cycloalkyl group having 3 to 12 carbon atoms or an optionally substituted aryl group, or an optionally substituted 5-membered or 6-membered heterocyclic radical which additionally can be fused to a benzene ring,are obtained in high yields by reacting carboxylic acid anhydrides of the formula R--CO--O--CO--R (II) with trimethylsilyl cyanide, (CH.sub.3).sub.3 Si--CN (III), if appropriate in the presence of a catalyst and, if appropriate, in the presence of a diluent, at a temperature between 50.degree. and 250.degree. C. The acyl cyanides can be used as intermediate products, for example, for the preparation of certain herbicidally active compounds of the triazinone series.Type: GrantFiled: October 22, 1982Date of Patent: June 19, 1984Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Eckart Kranz
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Patent number: 4451463Abstract: This invention relates to alcohol 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 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 alkyl, 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 hydrogen and R.sup.Type: GrantFiled: March 1, 1982Date of Patent: May 29, 1984Assignee: Imperial Chemical Industries PLCInventor: Michael S. Large
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Patent number: 4450169Abstract: Novel esters of the formula ##STR1## wherein R is selected from the group consisting of ##STR2## W is selected from the group consisting of hydrogen and --CN, Z is selected from the group consisting of --CH.sub.2 -- and --O--, and is attached to a carbon atom included between a nitrogen and the sulfur atom of Y and Y is selected from the group consisting of thiazolyl or thiadiazolyl connected to ##STR3## at one of its available positions.Type: GrantFiled: February 25, 1982Date of Patent: May 22, 1984Assignee: Roussel UclafInventors: Francois Nezot, Pierre Girault, Jean Tessier, Jacques Martel
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Patent number: 4447429Abstract: This invention relates to novel cephem compounds of high antimicrobial activity of the formula ##STR1## wherein R.sup.1 is amino or a protected amino,R.sup.2 is lower alkyl,R.sup.3 is hydrogen or lower alkyl,R.sup.4 is hydrogen, acyloxy(lower)alkyl or acylthio(lower)alkyl andR.sup.5 is carboxy or a protected carboxy.Type: GrantFiled: December 5, 1980Date of Patent: May 8, 1984Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
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Patent number: 4446142Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is hydrogen, halogen, or alkyl, R.sup.2 is halogen or alkyl, R.sup.3 is hydrogen, acyl, or saturated or unsaturated alkyl, R.sup.4 and R.sup.5 are individually hydrogen, or alkyl, wherein all alkyl and acyl groups are branched or straight-chain and each contains 1 to 4 carbon atoms, X is oxygen, nitrogen, or sulfur, Y is oxygen or nitrogen, and --X--Y-- is --O--N--, --N--O--, or --S--N--, or salts of the above, with certain exceptions. Methods of preparation of the compounds, as well as their use as anti-hypertensives are also disclosed.Type: GrantFiled: June 26, 1981Date of Patent: May 1, 1984Assignee: Beiersdorf AktiengesellschaftInventors: Erich Cohnen, Ben Armah
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Patent number: 4440775Abstract: The compounds are novel N-substituted-N'-heterocyclic alkylthioureas, guanidines and 1-nitro-2,2-diaminoethylene compounds which are histamine H.sub.2 -antagonists.Type: GrantFiled: June 18, 1982Date of Patent: April 3, 1984Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin, Geoffrey R. Owen, Rodney C. Young
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Patent number: 4438127Abstract: Amidinoformic acids and amidinosulphinic acids which are histamine H.sub.2 -antagonists. Two specific compounds of the present invention are N-[2-(5-methyl-4-imidazolylmethylthio)-ethyl]amidinoformic acid and N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amidiniosulphinic acid.Type: GrantFiled: March 7, 1983Date of Patent: March 20, 1984Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
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Patent number: 4435567Abstract: A process for the preparation of substituted urea derivatives, and compositions and concentrates for the same purpose are disclosed. According to the process the substituted urea derivatives of formula (I) ##STR1## wherein R is hydrogen, alkyl, aryl, cycloalkyl or aralkyl, R.sup.1 and R.sup.2 are hydrogen, alkyl, alkenyl, alkinyl, alkoxy, oxyalkyl, cycloalkyl, aralkyl, alkoxycarbonylalkyl, aryl or heteroaryl, or R.sup.1 and R.sup.Type: GrantFiled: December 28, 1981Date of Patent: March 6, 1984Assignee: Chinoin Gyogyszer es Vesgyeszeti Termekek Gyara R. T.Inventors: Gyorgy Lugosi, Antal Simay, Janos Bodnar, Laszlo Simandi, Eva Somfai
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Patent number: 4432897Abstract: The cationic triazene dyestuffs of the general formula ##STR1## wherein B denotes alkylmercapto, arylmercapto or a radical of the formula ##STR2## R denotes hydrogen or an alkyl, alkenyl, acyl, cycloalkyl, aryl, aralkyl, amino, alkylamino, dialkylamino, arylamino, aralkylamino or heterocyclic radical andR.sub.1 denotes hydrogen or an alkyl, alkenyl or aralkyl radical, orR and R.sub.1 are bonded to a heterocyclic structure,R.sub.2 and R.sub.3 denote an alkyl, alkenyl, alkinyl or aralkyl radical, or one of the radicals R.sub.2 or R.sub.3 also denotes hydrogen, orR.sub.3 is bonded to the o-position of A,A denotes an aryl radical andAn.sup.(-) denotes an anion,and wherein the cyclic and acyclic radicals can contain non-ionic substituents and/or a carboxyl group, can be used for dyeing and printing natural and synthetic materials.Type: GrantFiled: November 16, 1981Date of Patent: February 21, 1984Assignee: Bayer AktiengesellschaftInventor: Hauke Furstenwerth
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Patent number: 4427688Abstract: N-Substituted 2-methylnaphthylamides of the formula ##STR1## where R.sup.1 and R.sup.2 have the meanings given in the description, their preparation and their use for controlling fungi.Type: GrantFiled: May 13, 1982Date of Patent: January 24, 1984Assignee: BASF AktiengesellschaftInventors: Costin Rentzea, Bernd Zeeh, Eberhard Ammermann, Gerhard Hamprecht, Ernst-Heinrich Pommer
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Patent number: 4425340Abstract: This invention relates to new cephem and cepham compounds of high antimicrobial activity of the formula: ##STR1## wherein R.sup.1 is amino or a protected amino,R.sup.2 is hydrogen, acyl, aryl which may be substituted with suitable substituent(s), lower alkyl substituted with suitable substituent(s), lower alkenyl, lower alkynyl, cycloalkyl which may be substituted with suitable substituent(s), cyclo(lower)alkenyl, or S or O containing 5-membered heterocyclic group substituted with oxo group(s),R.sup.3 is hydrogen or lower alkyl,R.sup.4 is hydrogen, acyloxy(lower)alkyl; acylthio(lower) alkyl; pyridinium(lower)alkyl which may be substituted with suitable substituent(s); a heterocyclicthio(lower)alkyl which may be substituted with suitable substituent(s); lower alkyl;l halogen; hydroxy; thiazolium(lower)alkyl which may be substituted with suitable substituent(s); or lower alkoxy; R.sup.5 is carboxy or a protected carboxy, wherein R.sup.5 is COO.sup.- when R.sup.Type: GrantFiled: October 22, 1981Date of Patent: January 10, 1984Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
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Patent number: 4416683Abstract: 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: September 14, 1981Date of Patent: November 22, 1983Assignee: Eli Lilly and CompanyInventor: Kenneth W. Burow, Jr.
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Patent number: 4405621Abstract: The compounds are C.sub.2 -C.sub.8 straight chain alkanes terminally substituted, symmetrically or unsymmetrically, by N-(N'-substituted guanidino), N-(N',N"-disubstituted guanidino), N-(N'-substituted thioureido), N-(nitromethylene amidino) or S-(N-substituted isothioureido)groups. Two compounds of the invention are 1,3-bis-[N'-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidino]propane and 1,3-bis-[S-(N-2-(5-methyl-4-imidazolylmethylthio)ethyl)isothioureido]p ropane. The compounds of this invention are inhibitors of H-2 histamine receptors.Type: GrantFiled: June 11, 1981Date of Patent: September 20, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin
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Patent number: 4395419Abstract: Amidinoformic acids and amidinosulphinic acids which are histamine H.sub.2 -antagonists. A specific compound of this invention is N-[2-(3-(1,2,5)-thiadiazolylmethylthio)ethyl]amidinoformic acid.Type: GrantFiled: August 10, 1981Date of Patent: July 26, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
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Patent number: 4375472Abstract: Amidinosulphonic acid derivatives carrying an unsaturated nitrogen heterocycle-containing substituent, representative of which are N-methyl-N'[2-(5-methyl-4-imidazolylmethylthio)- ethyl] amidinosulphonic acid and N-methyl-N'-[2-(3-chloropyrid-2-ylmethylthio) ethyl] amidinosulphonic acid, are histamine H.sub.2 -receptor antagonists.Type: GrantFiled: November 24, 1980Date of Patent: March 1, 1983Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Rodney C. Young, Zev Tashma
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Patent number: 4370498Abstract: .alpha.-Ketocarboxylic acid N-acylamides of the formulaR.sup.1 --CO--CO--NH--CO--R.sup.2in whichR.sup.1 is an optionally substituted aliphatic radical with up to 12 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 10 carbon atoms, an optionally substituted heterocyclic radical, andR.sup.2 is an optionally substituted aliphatic radical with up to 8 carbon atoms or an optionally substituted phenyl radical,are prepared by reacting an acyl cyanide of the formulaR.sup.1 --CO--CNwith a carboxylic acid anhydride of the formulaR.sup.2 --CO--O--CO--R.sup.2in the presence of a strong acid, and then adding water to the reaction mixture. The products can be used directly in the synthesis of known herbicides.Type: GrantFiled: February 19, 1981Date of Patent: January 25, 1983Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Heinz U. Blank
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Patent number: 4360479Abstract: This invention relates to a new process for the preparation of acyl cyanides of the general formulaR.sup.1 --CO--CN (I)wherein R.sup.1 is an optionally substituted alkyl radical up to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring, which process comprises reacting a carboxylic acid anhydride of the formulaR.sup.1 --CO--O--CO--R.sup.1 (II)with an alpha-hydroxynitrile of the formula ##STR1## in which R.sup.2 and R.sup.3 are identical or different and represent a hydrogen atom, an optionally substituted alkyl radical with 1 to 18 carbon atoms, an optionally substituted cycloalkyl radical with 3 to 12 carbon atoms, an optionally substituted aryl radical or an optionally substituted 5- or 6-membered heterocyclic radical, which can additionally also be fused with a benzene ring.Type: GrantFiled: June 24, 1981Date of Patent: November 23, 1982Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Hans Kratzer, Manfred Lenthe
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Patent number: 4353920Abstract: Disclosed are selected 3-trihalomethyl-5-ureido-1,2,4-oxadiazole and -1,2,4-thiadiazole compounds of the formula: ##STR1## wherein X is either Cl or F and Y is either O or S. These compounds are shown to be effective against agricultural viruses.Type: GrantFiled: December 24, 1981Date of Patent: October 12, 1982Assignee: Olin CorporationInventors: Walter A. Gay, Elizabeth A. Twohig
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Patent number: 4345100Abstract: A process for the preparation of an .alpha.-ketocarboxylic acid N-tert.-butylamide of the formulaR--CO--CO--NH--C(CH.sub.3).sub.3in whichR is an aliphatic radical with up to 8 carbon atoms, a cycloalkyl radical with 3 to 6 carbon atoms, a phenyl or naphthyl radical or a heterocyclic radical,comprising reacting an acyl cyanide of the formulaR--CO--CNwith tert.-butyl methyl ether of the formula(CH.sub.3).sub.3 C--O--CH.sub.3at a temperature between about 0.degree. and 80.degree. C. in the presence of an acid which is capable of activating the ether of formula (III) under the reaction conditions to give a tert.-butyl carbonium ion, and then hydrolyzing the reaction mixture. Advantageously the acyl cyanide is pivaloyl cyanide or benzoyl cyanide and is reacted with an approximately equimolar amount of the ether in the presence of about 1.1 to 1.5 times the molar amount of concentrated sulphuric acid as the activating acid. The products are useful as intermediates in the synthesis of known herbicides.Type: GrantFiled: January 2, 1981Date of Patent: August 17, 1982Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Heinz U. Blank
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Patent number: 4343945Abstract: Disclosed are selected 5-benzamido-3-trichloromethyl-1,2,4-thiadiazole compounds of the formula: ##STR1## wherein R is phenyl which is unsubstituted or substituted by at least one member selected from the group consisting of lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, nitro and halo. These compounds are shown to have post-emergence herbicidal, fungicidal and insecticidal properties.Type: GrantFiled: August 13, 1981Date of Patent: August 10, 1982Assignee: Olin CorporationInventor: Walter A. Gay
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Patent number: 4342765Abstract: Guanidine derivatives which are histamine H-2 antagonists and which inhibit gastric acid secretion. These derivatives have the formula: ##STR1## in which X is oxygen or sulphur;Y is nitrogen or a CH radical;n is 1, 2, 3 or 4;m is 0 or 1;R.sup.1 is, for example, hydrogen or alkyl of 1-6 carbons; andR.sup.2 is, for example, ##STR2## and are characterized by the guanidino and cycloalkyl substituents which are attached directly to the heterocyclic ring.Type: GrantFiled: January 16, 1980Date of Patent: August 3, 1982Assignee: Imperial Chemical Industries LimitedInventors: Derrick F. Jones, Keith Oldham
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Patent number: 4338119Abstract: Novel N-Diazolylalkyl-haloacetanilides of the formula ##STR1## wherein A is oxygen, sulphur or the grouping >NR,whereinR 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: September 10, 1979Date of Patent: July 6, 1982Assignee: Bayer AktiengesellschaftInventors: Jorg Stetter, Klaus Ditgens, Rudolf Thomas, Ludwig Eue, Robert R. Schmidt
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Patent number: 4337081Abstract: Disclosed are selected 5-amido-3-trihalomethyl-1,2,4-thiadiazole compounds of the formula: ##STR1## wherein R.sub.1 is CCl.sub.3 or CF.sub.3 ; R.sub.2 is hydrogen, a lower alkyl group of 1 to 4 carbon atoms or an aryl group having 6 to 8 carbon atoms; and R.sub.3 is a lower alkyl group having from 2 to 4 carbon atoms, an aryl group having 6 to 8 carbon atoms, or CX.sub.3, where X is H, Cl, F or OCH.sub.3. These compounds are shown to have post-emergence herbicidal properties.Type: GrantFiled: January 23, 1979Date of Patent: June 29, 1982Assignee: Olin CorporationInventor: Walter A. Gay
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Patent number: 4332949Abstract: The invention relates to a thiadiazole derivative of the formula I: ##STR1## in which Y is O, S, CH.sub.2, SO or a direct bond; m is 0 to 4 and n is 1 to 4 provided that when Y is S, O or SO m is 1 to 4, and when Y is O or SO n is 2 to 4; R.sup.1 is H or (C.sub.1-10)alkyl; A is 3,4-dioxocyclobuten-1,2-diyl or C.dbd.Z in which Z is O, S, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.2, NCO.sub.2 R.sup.2, NSO.sub.2 R.sup.2 or NR.sup.3 in which R.sup.2 is (C.sub.1-6)alkyl or (C.sub.6-12)aryl and R.sup.3 is H or (C.sub.1-6)alkyl; B is (C.sub.1-6)alkoxy, (C.sub.1-6)alkylthio or NR.sup.4 R.sup.5 in which R.sup.4 and R.sup.5 are independently H, (C.sub.1-10)alkyl, C.sub.3-6 (alkenyl), (C.sub.3-6)alkynyl, (C.sub.2-6)(primary hydroxy)alkyl, (C.sub.2-6)(primary amino)alkyl or (C.sub.3-6)cycloalkyl or R.sup.4 and R.sup.5 are joined to form a 5- or 6- membered saturated ring optionally containing an additional O or NH: and the salts thereof.Type: GrantFiled: August 1, 1980Date of Patent: June 1, 1982Assignees: Imperial Chemical Industries PLC, ICI Americas Inc.Inventors: Tobias O. Yellin, Derrick M. Mant
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Patent number: 4332798Abstract: 7-Substituted-3-cephem and cepham-4-carboxylic acids of formula (I) ##STR1## wherein R.sup.1 is amino or a protected amino, R.sup.2 is hydrogen, acyl, aryl which may be substituted with suitable substituent(s), lower alkyl substituted with suitable substituent(s), lower alkenyl, lower alkynyl, cycloalkyl which may be substituted with suitable substituent(s), cyclo(lower)alkenyl, or S- or O-containing 5-membered heterocyclic group substituted with oxo group(s).R.sup.3 is hydrogen or lower alkyl,R.sup.4 is hydrogen; acyloxy(lower)alkyl; acylthio(lower)alkyl pyridinium(lower)alkyl which may be substituted with suitable substituent(s); a heterocyclicthio(lower)alkyl which may be substituted with suitable substituent(s); lower alkyl; halogen; or hydroxy; andR.sup.5 is carboxy or a protected carboxy wherein R.sup.5 is COO-- when R.sup.4 is pyridinium(lower)alkyl which may be substituted with suitable substituent(s), and the heavy solid line means single or double bond, have useful antibiotic properties.Type: GrantFiled: January 30, 1980Date of Patent: June 1, 1982Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
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Patent number: 4331665Abstract: 7-Substituted-3-cephem and cepham-4-carboxylic acids represented by the following formula (I): ##STR1## wherein R.sup.1 is amino or a protected amino,R.sup.2 is hydrogen, acyl, aryl which may be substituted with suitable substituent(s), lower alkyl substituted with suitable substituent(s), lower alkenyl, lower alkynyl, cycloalkyl which may be substituted with suitable substituent(s), cyclo(lower)alkenyl, or S or O containing 5-membered heterocyclic group substituted with oxo group(s),R.sup.3 is hydrogen or lower alkyl,R.sup.4 is hydrogen; acyloxy(lower)alkyl); acylthio(lower)alkyl; pyridinium(lower)alkyl which may be substituted with suitable substituent(s); a heterocyclicthio(lower)alkyl which may be substituted with suitable substituent(s); lower alkyl; halogen; or hydroxy; and,R.sup.5 is carboxy or a protected carboxy, wherein R.sup.5 is COO.sup.- when R.sup.Type: GrantFiled: March 7, 1980Date of Patent: May 25, 1982Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
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Patent number: 4323503Abstract: Novel substituted 2,3-alkylene bis (oxy) benzamides and derivatives thereof are disclosed. Also disclosed is a method for producing said compounds. The compounds have anxiolytic, psychostimulant, disinhibiting and thymoanaleptic properties useful therapeutically in the psychofunctional field, particularly in gastro-enterology, cardiology, urology, rheumatology and gynaecology.Type: GrantFiled: June 12, 1979Date of Patent: April 6, 1982Assignee: Societe d'Etudes Scientifiques et Industrielles de L'ile-de-FranceInventors: Michel Thominet, Gerard Bulteau, Jacques Acher, Claude Collignon
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Patent number: 4312664Abstract: Novel herbicidal composition comprising(1) a herbicidally active acetanilide and(2) as an antidote against damage to crop plants, N,N-diallyl-dichloroacetamide of the formula ##STR1##Type: GrantFiled: June 4, 1979Date of Patent: January 26, 1982Assignee: Bayer AktiengesellschaftInventors: Robert R. Schmidt, Wilfried Faust
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Patent number: 4309435Abstract: The invention relates to a guanidine derivative of the formula I: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 Iin which Y.sup.1 and Y.sup.2 are O, S, direct bonds, CH.sub.2 or SO; m and p are 0 to 4, n and q are 1 to 4, provided that when Y.sup.1 or Y.sup.2 is O, S or SO, m or p is 1 to 4 and provided that when Y.sup.1 or Y.sup.2 is O or SO, n or q is 2 to 4; one of R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen or C.sub.(1-6) alkyl; A is 3,4-dioxocyclobuten-1,2-diyl or C.dbd.Z in which Z is S, O, NCN, NNO.sub.2, CHNO.sub.2, NCONH.sub.2, C(CN).sub.2, NCOR.sup.3, NCO.sub.2 R.sup.3 NSO.sub.2 R.sup.3 or NR.sup.4 in which R.sup.3 is C.sub.(1-6) alkyl or C.sub.(6-12) aryl and R.sup.4 is hydrogen or C.sub.(1-6) alkyl or when R.sup.1 and R.sup.2 are hydrogen A is-A.sup.1 -E.sup.1 -G-E.sup.2 -A.sup.2 - IIin which A.sup.1 and A.sup.2 are 3,4-dioxocyclobuten-1,2-diyl or C.dbd.Z.sup.1 and C.dbd.Z.sup.2 in which Z.sup.Type: GrantFiled: October 10, 1979Date of Patent: January 5, 1982Assignees: Imperial Chemical Industries Ltd., ICI Americas Inc.Inventors: Tobias O. Yellin, David J. Gilman
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Patent number: 4308275Abstract: Amidinoformic acids and amidinosulphinic acids which are histamine H.sub.2 -antagonists. Two specific compounds of the present invention are N-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amidinoformic acid and N-methyl-N'-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amidinosulphinic acid.Type: GrantFiled: August 10, 1979Date of Patent: December 29, 1981Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
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Patent number: 4302583Abstract: Novel process for the preparation of a monomeric acyl cyanide of the general formula ##STR1## in which R represents optionally substituted alkyl with up to 8 carbon atoms, optionally substituted cycloalkyl with 3 to 12 carbon atoms, optionally substituted aryl or an optionally substituted 5-membered or 6-membered heterocyclic radical, which optionally can be fused with a benzene ring,which process comprises heating the corresponding dimeric acyl cyanide of the general formula ##STR2## in which R has the meaning stated above, to a temperature of from 50.degree. to 300.degree. C. in the presence of a compound having a basic reaction and rapidly removing the monomeric acyl cyanide (I) formed from the reaction mixture.Type: GrantFiled: April 25, 1979Date of Patent: November 24, 1981Assignee: Bayer AktiengesellschaftInventors: Kurt Findeisen, Karl-Heinz Linker
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Patent number: 4284584Abstract: Acyl cyanides of the formula ##STR1## in which R represents alkyl or substituted alkyl of from 1 to 8 carbon atoms, cycloalkyl or substituted cycloalkyl of from 3 to 12 carbon atoms, aryl or substituted aryl; or an optionally substituted 5-membered or 6-membered heterocyclic radical which can also be fused with a benzene ringare prepared by reacting the corresponding carboxylic acid anhydride in the presence of a carboxylic acid halide with an alkali metal cyanide or anhydrous acid, at a temperature of between 50.degree. and 300.degree. C.Type: GrantFiled: December 8, 1978Date of Patent: August 18, 1981Assignee: Bayer AktiengesellschaftInventor: Kurt Findeisen
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Patent number: 4284787Abstract: Triazoles of the formula ##STR1## in which R.sub.1 is hydrogen or a substituent of the type indicated in the description,R.sub.2 is a substituent, orR.sub.1 and R.sub.2, together with the triazole ring carbon atoms to which they are bonded, form a carbocyclic or heterocyclic ring, andR.sub.3 is the radical of an aromatic-carbocyclic or aromatic-heterocyclic system,are obtained in an elegant manner when compounds of the formula II are treated with a basic compound, preferably a tertiary amine. The triazoles are, inter alia, valuable starting materials for the preparation of optical brighteners.Type: GrantFiled: April 11, 1979Date of Patent: August 18, 1981Assignee: Bayer AktiengesellschaftInventors: Hans Knupfer, Carl-Wolfgang Schellhammer
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Patent number: 4284640Abstract: The compounds are ethylene derivatives which are inhibitors of histamine activity, in particular, inhibitors of H-2 histamine receptors. A compound of this invention is 1-nitro-2-methylamino-2-[2-((4-methyl-5-imidazolyl)methylthio)ethylamino]e thylene.Type: GrantFiled: February 4, 1980Date of Patent: August 18, 1981Assignee: Smith Kline & French Laboratories LimitedInventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin, Hunter D. Prain
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Patent number: 4263312Abstract: Disclosed are selected 5-hydrazono-3-trichloromethyl-1,2,4-thiadiazole compounds of the formula: ##STR1## wherein R is a lower alkyl having 1 to 4 carbon atoms, phenyl, and substituted phenyl in which the said phenyl ring substituents are selected from lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, halo, hydroxy, nitro and mixtures thereof; and R' and R" are individually selected from hydrogen and lower alkyl having 1 to 4 carbon atoms. These compounds are shown to have foliar fungicidal activity.Type: GrantFiled: June 23, 1980Date of Patent: April 21, 1981Assignee: Olin CorporationInventor: Lawrence E. Katz
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Patent number: 4255425Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.Type: GrantFiled: November 13, 1978Date of Patent: March 10, 1981Assignee: Smith Kline & French Laboratories LimitedInventor: George R. White
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Patent number: 4254265Abstract: Disclosed are selected 5-trichloromethylthioamino derivatives of 3-trihalomethyl-1,2,4-thiadiazole compounds which have the formula: ##STR1## wherein R.sub.1 is CCl.sub.3 or CF.sub.3 ; and wherein R.sub.2 is hydrogen, a lower alkyl having 1 to 4 carbon atoms, phenyl and substituted phenyl wherein said substituents are lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, amino, nitro, halo and mixtures thereof. These compounds are diclosed to be agricultural fungicides.Type: GrantFiled: April 21, 1980Date of Patent: March 3, 1981Assignee: Olin CorporationInventors: Walter A. Gay, Elizabeth A. Twohig
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Patent number: 4247550Abstract: The invention relates to a series of new compounds, salts thereof and to methods for the preparation of the compounds which have the general formula ##STR1## in which R.sub.1 stands for an unsubstituted or substituted phenoxy, phenylthio, benzyl, phenylsulfinyl, or anilino radical;R.sub.2 stands for a --YR.sub.2 ' radical, in which Y represents --O--, --S--, or --NH--, and R.sub.2 ' represents C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or -alkynyl; or methyl or ethyl substituted with phenyl, furyl, thienyl or pyridyl;R.sub.3 and R.sub.4 which can be the same or different, and unsubstituted or substituted, stand for hydrogen or for a straight or branched C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl or -alkynyl radical, a C.sub.5 -C.sub.7 -cycloalkyl, a phenyl, or a 5-, 6- or 7-membered heterocyclic ring system containing not more than two hetero atoms selected from the group consisting of oxygen, sulphur and nitrogen, or for a C.sub.1 -C.sub.Type: GrantFiled: December 21, 1977Date of Patent: January 27, 1981Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)Inventors: Peter W. Feit, Ole B. T. Nielsen, Herta Bruun, Claus A. S. Bretting