1,2,4-thiadiazoles (including Hydrogenated) Patents (Class 548/128)
  • Patent number: 4537903
    Abstract: 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: Grant
    Filed: October 12, 1983
    Date of Patent: August 27, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
  • Patent number: 4532250
    Abstract: 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: Grant
    Filed: November 23, 1983
    Date of Patent: July 30, 1985
    Assignee: American Hospital Supply Corporation
    Inventors: David M. Stout, Diane M. Yamamoto
  • Patent number: 4504304
    Abstract: 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: Grant
    Filed: August 29, 1983
    Date of Patent: March 12, 1985
    Assignee: Shell Oil Company
    Inventors: Herbert Estreicher, George B. Payne
  • Patent number: 4500340
    Abstract: 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: Grant
    Filed: November 22, 1982
    Date of Patent: February 19, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Becker, Hans Theobald, Ulrich Schirmer, Wolfgang Spiegler, Walter Seufert, Bruno Wuerzer
  • Patent number: 4496571
    Abstract: 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: Grant
    Filed: March 1, 1982
    Date of Patent: January 29, 1985
    Assignees: ICI Americas Inc., Imperial Chemical Industries, PLC
    Inventors: Tobias O. Yellin, David J. Gilman, Philip N. Edwards, Michael S. Large, Derrick F. Jones, Keith Oldham
  • Patent number: 4488895
    Abstract: 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: Grant
    Filed: January 28, 1982
    Date of Patent: December 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Klaus Ditgens, Rudolf Thomas, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4468515
    Abstract: This invention relates to thiadiazolyl compounds useful as intermediates in the preparation of novel cephem compounds of high antimicrobial activity.
    Type: Grant
    Filed: November 25, 1981
    Date of Patent: August 28, 1984
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4463005
    Abstract: 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: Grant
    Filed: March 10, 1982
    Date of Patent: July 31, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4461900
    Abstract: 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: Grant
    Filed: March 14, 1983
    Date of Patent: July 24, 1984
    Assignee: American Home Products Corporation
    Inventor: Dieter H. Klaubert
  • Patent number: 4460584
    Abstract: 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: Grant
    Filed: March 9, 1982
    Date of Patent: July 17, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4460580
    Abstract: 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: Grant
    Filed: June 24, 1982
    Date of Patent: July 17, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Franz Ostermayer, Markus Zimmermann
  • Patent number: 4456565
    Abstract: 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: Grant
    Filed: July 14, 1983
    Date of Patent: June 26, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Herbert Schwarz
  • Patent number: 4455264
    Abstract: 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: Grant
    Filed: October 22, 1982
    Date of Patent: June 19, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Eckart Kranz
  • Patent number: 4451463
    Abstract: 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: Grant
    Filed: March 1, 1982
    Date of Patent: May 29, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Michael S. Large
  • Patent number: 4450169
    Abstract: 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: Grant
    Filed: February 25, 1982
    Date of Patent: May 22, 1984
    Assignee: Roussel Uclaf
    Inventors: Francois Nezot, Pierre Girault, Jean Tessier, Jacques Martel
  • Patent number: 4447429
    Abstract: 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: Grant
    Filed: December 5, 1980
    Date of Patent: May 8, 1984
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4446142
    Abstract: 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: Grant
    Filed: June 26, 1981
    Date of Patent: May 1, 1984
    Assignee: Beiersdorf Aktiengesellschaft
    Inventors: Erich Cohnen, Ben Armah
  • Patent number: 4440775
    Abstract: 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: Grant
    Filed: June 18, 1982
    Date of Patent: April 3, 1984
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Geoffrey R. Owen, Rodney C. Young
  • Patent number: 4438127
    Abstract: 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: Grant
    Filed: March 7, 1983
    Date of Patent: March 20, 1984
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
  • Patent number: 4435567
    Abstract: 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: Grant
    Filed: December 28, 1981
    Date of Patent: March 6, 1984
    Assignee: Chinoin Gyogyszer es Vesgyeszeti Termekek Gyara R. T.
    Inventors: Gyorgy Lugosi, Antal Simay, Janos Bodnar, Laszlo Simandi, Eva Somfai
  • Patent number: 4432897
    Abstract: 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: Grant
    Filed: November 16, 1981
    Date of Patent: February 21, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hauke Furstenwerth
  • Patent number: 4427688
    Abstract: 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: Grant
    Filed: May 13, 1982
    Date of Patent: January 24, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Bernd Zeeh, Eberhard Ammermann, Gerhard Hamprecht, Ernst-Heinrich Pommer
  • Patent number: 4425340
    Abstract: 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: Grant
    Filed: October 22, 1981
    Date of Patent: January 10, 1984
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4416683
    Abstract: 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: Grant
    Filed: September 14, 1981
    Date of Patent: November 22, 1983
    Assignee: Eli Lilly and Company
    Inventor: Kenneth W. Burow, Jr.
  • Patent number: 4405621
    Abstract: 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: Grant
    Filed: June 11, 1981
    Date of Patent: September 20, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4395419
    Abstract: 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: Grant
    Filed: August 10, 1981
    Date of Patent: July 26, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
  • Patent number: 4375472
    Abstract: 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: Grant
    Filed: November 24, 1980
    Date of Patent: March 1, 1983
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Rodney C. Young, Zev Tashma
  • Patent number: 4370498
    Abstract: .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: Grant
    Filed: February 19, 1981
    Date of Patent: January 25, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Heinz U. Blank
  • Patent number: 4360479
    Abstract: 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: Grant
    Filed: June 24, 1981
    Date of Patent: November 23, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Hans Kratzer, Manfred Lenthe
  • Patent number: 4353920
    Abstract: 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: Grant
    Filed: December 24, 1981
    Date of Patent: October 12, 1982
    Assignee: Olin Corporation
    Inventors: Walter A. Gay, Elizabeth A. Twohig
  • Patent number: 4345100
    Abstract: 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: Grant
    Filed: January 2, 1981
    Date of Patent: August 17, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Heinz U. Blank
  • Patent number: 4343945
    Abstract: 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: Grant
    Filed: August 13, 1981
    Date of Patent: August 10, 1982
    Assignee: Olin Corporation
    Inventor: Walter A. Gay
  • Patent number: 4342765
    Abstract: 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: Grant
    Filed: January 16, 1980
    Date of Patent: August 3, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4338119
    Abstract: 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: Grant
    Filed: September 10, 1979
    Date of Patent: July 6, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Klaus Ditgens, Rudolf Thomas, Ludwig Eue, Robert R. Schmidt
  • Patent number: 4337081
    Abstract: 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: Grant
    Filed: January 23, 1979
    Date of Patent: June 29, 1982
    Assignee: Olin Corporation
    Inventor: Walter A. Gay
  • Patent number: 4332949
    Abstract: 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: Grant
    Filed: August 1, 1980
    Date of Patent: June 1, 1982
    Assignees: Imperial Chemical Industries PLC, ICI Americas Inc.
    Inventors: Tobias O. Yellin, Derrick M. Mant
  • Patent number: 4332798
    Abstract: 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: Grant
    Filed: January 30, 1980
    Date of Patent: June 1, 1982
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4331665
    Abstract: 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: Grant
    Filed: March 7, 1980
    Date of Patent: May 25, 1982
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Tsutomu Teraji, Kazuo Sakane, Jiro Goto
  • Patent number: 4323503
    Abstract: 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: Grant
    Filed: June 12, 1979
    Date of Patent: April 6, 1982
    Assignee: Societe d'Etudes Scientifiques et Industrielles de L'ile-de-France
    Inventors: Michel Thominet, Gerard Bulteau, Jacques Acher, Claude Collignon
  • Patent number: 4312664
    Abstract: 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: Grant
    Filed: June 4, 1979
    Date of Patent: January 26, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Robert R. Schmidt, Wilfried Faust
  • Patent number: 4309435
    Abstract: 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: Grant
    Filed: October 10, 1979
    Date of Patent: January 5, 1982
    Assignees: Imperial Chemical Industries Ltd., ICI Americas Inc.
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4308275
    Abstract: 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: Grant
    Filed: August 10, 1979
    Date of Patent: December 29, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Rodney C. Young
  • Patent number: 4302583
    Abstract: 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: Grant
    Filed: April 25, 1979
    Date of Patent: November 24, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Findeisen, Karl-Heinz Linker
  • Patent number: 4284584
    Abstract: 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: Grant
    Filed: December 8, 1978
    Date of Patent: August 18, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventor: Kurt Findeisen
  • Patent number: 4284787
    Abstract: 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: Grant
    Filed: April 11, 1979
    Date of Patent: August 18, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans Knupfer, Carl-Wolfgang Schellhammer
  • Patent number: 4284640
    Abstract: 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: Grant
    Filed: February 4, 1980
    Date of Patent: August 18, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin, Hunter D. Prain
  • Patent number: 4263312
    Abstract: 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: Grant
    Filed: June 23, 1980
    Date of Patent: April 21, 1981
    Assignee: Olin Corporation
    Inventor: Lawrence E. Katz
  • Patent number: 4255425
    Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: March 10, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventor: George R. White
  • Patent number: 4254265
    Abstract: 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: Grant
    Filed: April 21, 1980
    Date of Patent: March 3, 1981
    Assignee: Olin Corporation
    Inventors: Walter A. Gay, Elizabeth A. Twohig
  • Patent number: 4247550
    Abstract: 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: Grant
    Filed: December 21, 1977
    Date of Patent: January 27, 1981
    Assignee: Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab)
    Inventors: Peter W. Feit, Ole B. T. Nielsen, Herta Bruun, Claus A. S. Bretting