Abstract: Dimercaptothiadiazole adducts of hydroxyl-containing unsaturated compounds and their borated analogues provide effective multifunctional friction reducing and corrosion inhibiting properties to various lubricating fluids when incorporated therein.
Type:
Grant
Filed:
June 18, 1981
Date of Patent:
May 10, 1983
Assignee:
Mobil Oil Corporation
Inventors:
Andrew G. Horodysky, Phillip S. Landis, Robert M. Gemmill, Jr.
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
Abstract: Bisamidines carrying one unsaturated nitrogen heterocyclo-containing substituent, representative of which i; 1-[N'-(2-(5-methyl-4-imidazolyl)methylthio)ethyl)guanidino]-8-[N'-methylgu anidino]octane, are histamine H.sub.2 -antagonists.
Type:
Grant
Filed:
March 27, 1981
Date of Patent:
February 8, 1983
Assignee:
Smith Kline & French Laboratories Limited
Abstract: The compounds are sulphoxides of heterocyclicthioalkylthioureas, ureas and guanidines which are useful to produce inhibition of histamine H-2 receptors.
Type:
Grant
Filed:
October 16, 1980
Date of Patent:
July 6, 1982
Assignee:
SmithKline & French Laboratories Limited
Abstract: 3-Nitro-2-substituted aminopyrroles are histamine H.sub.2 -receptor antagonists. The 2- position substituent is a fully-unsaturated heterocyclyl alkyl group preferably with alkyl group interrupted by sulfur or oxygen. The 4- and 5- positions of the pyrrole ring can also be substituted.
Type:
Grant
Filed:
June 16, 1980
Date of Patent:
May 25, 1982
Assignee:
Smith Kline & French Laboratories Limited
Abstract: This invention concerns certain substituted 1,3,4-thiadiazol-2-yl-4-hydroxy-1-methyl-2-imidazolidinones having herbicidal activity, their preparation, and the control of weeds therewith.
Abstract: Novel 2-amino-thiadiazole derivatives of the formula ##STR1## are described. In the formula, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl; R.sub.3 is hydrogen or the group --CO--R.sub.4, in which R.sub.4 is alkoxyalkyl, C.sub.3 -C.sub.6 cycloalkyl, or is C.sub.2 -C.sub.4 alkenyl each of which is unsubstituted or mono- or polysubstituted by halogen, or is furyl, thienyl, pyridyl or phenyl, each of which is unsubstituted or mono- to tetrasubstituted by C.sub.1 -C.sub.4 alkyl, halogen, cyano, nitro, alkoxy, alkylthio, alkylsulfonyl or amino. These compounds possess useful bactericidal properties and can be used in particular for controlling phytopathogenic bacteria without damaging the treated cultivated plants. In comparison to aminothiadiazoles of the prior art, the compounds of this invention cause no tetratogenic side-effects.
Type:
Grant
Filed:
May 7, 1980
Date of Patent:
August 25, 1981
Assignee:
Ciba-Geigy Corporation
Inventors:
Karl Gatzi, Hanspeter Baumann, Walter Kunz, Bernhard Gloor
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
Abstract: A process for preparing the compound 5-t-butyl-2-methylamino-1,3,4-thiadiazole, ##STR1## in high yield by the reaction of 4-methyl-3-thiosemicarbazide with pivalic acid in a solution containing both polyphosphoric acid and concentrated sulfuric acid, followed by neutralizing the reaction mixture with a neutralizing mixture comprising an organic solvent and an alkaline substance dissolved in water and separating 5-t-butyl-2-methylamino-1,3,4-thiadiazole from the organic phase.
Abstract: The compounds are N-(heterocyclomethylthioalkyl)derivatives of alkylguanidines, C-alkyl and C-aryl amidines and S-alkylisothioureas. The compounds may also have N'-lower alkyl or N'-(heterocyclomethylthioalkyl)substituents. Three compounds of the invention are S-methyl-N-[2-(5-methyl-4-imidazolylmethylthio)ethyl]isothiourea, N,N'-bis-[2-(5-methyl-4-imidazolymethylthio)ethyl]acetamidine, N,N'-bis-[2-(5-methyl-4-imidazolymethylthio)ethyl]N"-methylguanidine. The compounds of this invention are histamine H.sub.2 -antagonists.
Type:
Grant
Filed:
May 14, 1979
Date of Patent:
August 4, 1981
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Graham J. Durant, Charon R. Ganellin, Rodney C. Young
Abstract: Disclosed are azo dyes having the general formula ##STR1## in which R is hydrogen, --NO.sub.2, --CN, halogen, alkoxy, alkyl, alkoxycarbonyl, or CF.sub.3, and A is the residue of an aniline, tetrahydroquinoline or benzomorpholine disperse dye coupling component. These dyes produce red to blue shades on polyester fibers and exhibit one or more improved properties such as dyeability, light fastness, pH stability, build, and the like on polyester, polyamide and cellulose ester fibers.
Abstract: The disclosed compounds, such as 3-[5-[1-(2-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl- 2-imidazolidinone, are useful for preemergence and postemergence control of weeds, such as jimsonweed.
Abstract: The disclosed compounds, such as 3-[5-[1-(3,5-dichlorophenoxy) ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone, are useful for preemergence control of weeds, such as jimsonweed.
Abstract: Novel N-azolylalkyl-aniline compound of the formula ##STR1## in which A is oxygen, sulfur or the radical >NR.sup.2,R is hydrogen or alkyl,R.sup.1 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, halogen, optionally substituted aryl, optionally substituted aralkyl or the radicals --OR.sup.3, --SR.sup.3 or --NH.sup.2 R.sup.3,R.sup.2 is hydrogen, alkyl or optionally substituted aryl,R.sup.3 is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl or optionally substituted aralkyl,X is alkyl,Y is alkyl or halogen andn is 0, 1 or 2.
Type:
Grant
Filed:
February 9, 1979
Date of Patent:
May 12, 1981
Assignee:
Bayer Aktiengesellschaft
Inventors:
Jorg Stetter, Wilfried Draber, Rudolf Thomas, Winfried Lunkenheimer
Abstract: The present invention relates to certain new imidazo [2,1-b]-[1,3,4]-thiadiazole compounds, to the provision of pharmaceutical compositions containing said compounds and to the use of said compounds and compositions as antithrombotic agents and thrombolytic agents.
Type:
Grant
Filed:
May 10, 1979
Date of Patent:
May 5, 1981
Assignee:
Bayer Aktiengesellschaft
Inventors:
Harald Horstmann, Karl-August Meng, deceased, by Matthias Meng, legal representative, Friedel Seuter, Eike Moller
Abstract: The novel compound having the structural formula, ##STR1## which may be conveniently synthesized from readily available chemical substances is disclosed to be useful as a fungicide, particularly in combating fungus diseases of plants by application to soil or plant foliage.
Abstract: The disclosed compounds, such as 3-[5-[1-(4-chlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl- 2-imidazolidinone, are useful for preemergence and postemergence control of weeds, such as jimsonweeds.
Abstract: The compounds are substituted 2-amino-4-pyrimidones with a 5-(hydroxypyridylalkyl) substituent which are histamine H.sub.2 -antagonists. Two specific compounds are 2-[2-(3-bromo-2-pyridylmethylthio)ethylamino]-5-(2-hydroxy-4-pyridylmethyl )-4-pyrimidone and 2-[4-(3-methoxy-2-pyridyl)butylamino]-5-(2-hydroxy-4-pyridylmethyl)-4-pyri midone.
Type:
Grant
Filed:
April 24, 1979
Date of Patent:
March 10, 1981
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Thomas H. Brown, Graham J. Durant, Charon R. Ganellin
Abstract: The disclosed compounds such as 3-[5-[1-(2-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl- 2-imidazolidinone, control weeds preemergence and postemergence.
Abstract: The disclosed compounds such as 3-[5-[1-(2-nitrophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2 -imidazolidinone are useful for preemergence control of weeds such as jimsonweed.
Abstract: Certain sulfonamidothiadiazoles, metal complexes thereof and solutions of said compounds in essentially water-immiscible, liquid hydrocarbon solvents are disclosed. The sulfonamidothiadiazoles have the general structural formula: ##STR1## wherein R and A are as defined in the specification and claims hereof. Particular metal values are recovered from their aqueous solutions by using sulfonamidothiadiazoles dissolved in essentially water-immiscible, liquid hydrocarbon solvents. The extraction process involves contacting the metal value containing aqueous solution with the solution of the sulfonamidothiadiazole in essentially water-immiscible, liquid hydrocarbon solvent and stripping the metal from the loaded organic phase.
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
Abstract: A dyestuff of the general formula (I) ##STR1## in which R represents alkyl, alkenyl, cycloalkyl, aralkyl, aryl or, preferably, hydrogen, M represents hydrogen or a cation, Y represents a free or modified carboxyl group, Z represents a non-ionic substituent, n represents 0, 1 or 2, A represents a heterocyclic radical or an aromatic radical having negative substituents and B and C can carry further non-ionic substituents. The dyestuffs give brilliant red and yellow shades on polyester fibers.
Type:
Grant
Filed:
January 11, 1979
Date of Patent:
November 25, 1980
Assignee:
Ciba-Geigy Aktiengesellschaft
Inventors:
Hansrudolf Schwander, Christian Zickendraht
Abstract: Color photographic material is provided which contains at least one silver halide emulsion layer containing a yellow color coupler of the formula ##STR1## wherein G is the radical of a yellow coupler which is bonded to the heterocyclic ring by means of the active methylene group, Z is --CO-- or --SO.sub.2 --, M is hydrogen if Z is --CO--, or a substituent and R is hydrogen or a substituent.The new two-equivalent yellow couplers lead due to their improved reactivity (high maximum density), minimal fog and high fastness to light and outstanding spectral properties of the dyestuffs formed therefrom to a color photographic material of advantageous properties.
Type:
Grant
Filed:
April 27, 1978
Date of Patent:
October 21, 1980
Assignee:
Ciba-Geigy AG
Inventors:
Graham Evans, Mario Fryberg, Thomas Stauner, Paul Tschopp, David G. Leppard
Abstract: The disclosed compounds such as 3-[5-[1-(2-methylphenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl- 2-imidazolidinone, control weeds preemergence and postemergence.
Abstract: The proposed gastric secretion stimulator comprises an active principle which is 2-amino-5-(2-aminoethyl)-1,3,4-thiadiazole, and a pharmaceutical carrier for said active principle. The stimulator is used in the form of hydrochlorides. It displays a selective stimulating effect upon H.sub.2 -ceptors of secretory cells of the stomach and produces a maximum of gastric secretion, which is an important diagnostic factor. The gastric secretion stimulator of this invention is advantageous in that besides parenteral administration, it may be administered per os.
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:
September 6, 1978
Date of Patent:
July 1, 1980
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Graham J. Durant, Rodney C. Young, Zev Tashma
Abstract: The compounds are N-(heterocyclomethylthioalkyl) derivatives of alkylguanidines, C-alkyl and C-aryl amidines and S-alkylisothioureas. The compounds may also have N'-lower alkyl or N'(heterocyclomethylthioalkyl) substituents. Three compounds of the invention are S-methyl-N-[2-(5-methyl-4-imidazolylmethylthio)ethyl]isothiourea, N,N'-bis-[2-(5-methyl-4-imidazolylmethylthio)ethyl]acetamidine, N,N'-bis-[2-(5-methyl-4-imidazolylmethylthio)ethyl]N"-methylguanidine. The compounds of this invention are histamine H.sub.2 -antagonists.
Type:
Grant
Filed:
April 17, 1978
Date of Patent:
March 4, 1980
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Graham J. Durant, Charon R. Ganellin, Rodney C. Young
Abstract: 1-Alkyl-1-(1,3,4-thiadiazol-2-yl)-3-phenyl-ureas of the formula ##STR1## in which R.sup.1 is alkyl,R.sup.2 is phenyl or substituted phenyl, andX is hydrogen or halogen,which possess fungicidal properties.
Type:
Grant
Filed:
March 2, 1978
Date of Patent:
November 13, 1979
Assignee:
Bayer Aktiengesellschaft
Inventors:
Erik Regel, Paul-Ernst Frohberger, Volker Paul