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
Abstract: An improved process for the trimethylsilylation of organic compounds with at least one active hydrogen atom with hexamethyldisilazane, the improvement comprising effecting the reaction in the presence of 0.001 to 10 mole percent of a catalyst of the formulaX--NH--Y Iwherein X and Y are individually an electron-withdrawing group or when X is an electron-withdrawing group, Y is selected from the group consisting of hydrogen and trialkylsilyl of 1 to 6 carbon atoms or X and Y together with the nitrogen atom to which they are attached form a cyclic electron-withdrawing group and novel trimethylsilylated thiols of the formula ##STR1## wherein R is a 5-or 6-membered heterocycle having at least one nitrogen or sulfur heteroatom and optionally substituted with at least one member of the group consisting of alkyl of 1 to 6 carbon atoms, phenyl, trimethylsilyl, trimethylsilyloxycarbonylmethyl and alkylamino of 1 to 6 carbon atoms, and novel trimethylsilylated 3'-substituted cephalosporanic acid derivatives.
Type:
Grant
Filed:
July 6, 1981
Date of Patent:
August 23, 1983
Assignee:
Gist-Brocades N.V.
Inventors:
Cornelis A. Bruynes, Theodorus K. Jurriens
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
Abstract: 1-Aroyl-2-phenylamino-2-imidazolines of the general formula ##STR1## where R.sup.1 and R.sup.2 are identical or different and each is chlorine, bromine, fluorine, methyl, ethyl, methoxy, trifluoromethyl or cyano,R.sup.3 has the meanings given for R.sup.1 and R.sup.2 or is hydrogen andAr is an unsubstituted or substituted monocyclic or bicyclic heteroaromatic radical containing 1, 2 or 3 nitrogen and/or oxygen and/or sulfur atoms, their salts with physiologically tolerated acids, their preparation, and drugs containing these compounds.The compounds have, inter alia, a blood pressure-reducing action.
Type:
Grant
Filed:
March 3, 1981
Date of Patent:
June 21, 1983
Assignee:
BASF Aktiengesellschaft
Inventors:
Hans-Joachim May, Dieter Lenke, Josef Gries, Hans-Juergen Teschendorf, Wolfgang Worstmann
Abstract: A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxime derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts and the like), as desired, can be treated with these oxime derivatives, which are used as a dressing.Ar is a phenyl radical of the formula ##STR2## or Ar is also a 5-membered to 10-membered heterocyclic radical which contains not more than three identical or different hetero-atoms N, O and/or S and which can be bonded via a C.sub.1 - to C.sub.3 -aliphatic chain to the remainder of the molecule and which is substituted by R.sub.1, R.sub.2 or R.sub.3 and can be substituted by oxo or thiono; X is hydrogen, CN, halogen, C.sub.1 -C.sub.
Type:
Grant
Filed:
February 9, 1981
Date of Patent:
June 14, 1983
Assignee:
Ciba-Geigy Corporation
Inventors:
Haukur Kristinsson, Beat Muller, Johannes P. Pachlatko
Abstract: The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. A compound of this invention is N-cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-N"-[2-(2-thiazolyl methylthio)ethyl]guanidine.
Type:
Grant
Filed:
December 11, 1980
Date of Patent:
June 14, 1983
Assignee:
Smith Kline & French Laboratories Limited
Abstract: New thioloesters of the formula: ##STR1## wherein R.degree. represents hydrogen, alkyl, vinyl, cyanomethyl or a protecting radical, R' represents hydrogen or a protecting radical, R represents alkyl, L-2-amino-2-carboxyethyl, phenyl or various heterocyclic radicals, and their syn and anti isomers and mixtures thereof, and metal salts thereof and addition salts thereof with tertiary nitrogen-containing bases, are intermediates useful in the preparation of cephalosporins having anti-bacterial properties.
Type:
Grant
Filed:
February 10, 1981
Date of Patent:
May 24, 1983
Assignee:
Rhone Poulenc Industries
Inventors:
Daniel Farge, Pierre L. Roy, Claude Moutonnier, Jean-Francois Peyronel
Abstract: This invention relates to novel heterocyclic fungicides which are effective in controlling a broad spectrum of phytopathogenic fungi found in the four main classes of fungi namely Phycomycetes, Ascomycetes, Fungi Imperfecti, and Basidiomycetes. Certain of these compounds are especially effective in controlling sclerotial forming fungi such as Whetzelinia sclerotiorum=(Sclerotinia sclerotiorium) and Botrytis cinerea.
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: Tetrazole derivatives of the formula: ##STR1## wherein R.sup.1 is a lower alkykl, phenyl or a group of the formula: --S(O).sub.l --A--(X).sub.m --R.sup.3, and R.sup.2 is hydrogen, a lower alkyl, phenyl or a cycloalkyl when R.sup.1 is the group --S(O).sub.l --A--(X).sub.m --R.sup.3, or R.sup.2 is a group of the formula: --B--CO--R.sup.4 when R.sup.1 is a lower alkyl or phenyl and a pharmaceutically acceptable salt thereof, which have prophylactic or therapeutic activities against peptic and/or duodenal ulcers and are useful as an anti-ulcer drug; processes for the preparation of the tetrazole derivatives; and pharmaceutical composition containing said tetrazole derivatives.
Abstract: A method for production of novel antifungal 1,3,4-thiadiazole derivatives having a composition of the general formula ##STR1## wherein R.sub.1 and R.sub.2 are independently alkyl with from 1 to 6 carbon atoms, alkenyl with from 2 to 6 carbon atoms, alkinyl with from 2 to 6 carbon atoms or cycloalkyl with from 3 to 6 carbon atoms is provided. 1,3,4-thiadiazole derivatives of a composition of the general formula ##STR2## are reacted with a compound having the composition of the general formula R.sub.1 -SH resulting in compounds of a composition having the formula ##STR3## which in turn are oxidized with an organic or inorganic oxidant.
Type:
Grant
Filed:
August 12, 1980
Date of Patent:
January 18, 1983
Assignee:
Schering Aktiengesellschaft
Inventors:
Ludwig Nuesslein, Dietrich Baumert, Georg-Alexander Hoyer, Ernst A. Pieroh
Abstract: The invention relates to novel 1,3,4-thiadiazolyloxyphenylureas which possess herbicidal properties and which have good selectivity in different crops of cultivated plants. The novel phenylureas have the general formula I ##STR1## wherein X is hydrogen, halogen or trifluoromethyl,Y is hydrogen, C.sub.1 -C.sub.6 alkyl which can be interrupted by oxygen or substituted by halogen or cyano; C.sub.3 -C.sub.6 cycloalkyl, cyclopropylmethyl, phenyl which is unsubstituted or substituted by chlorine or C.sub.1 -C.sub.4 alkyl; or is C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl, or a sulfamoyl group --SO.sub.2 NR.sub.2 R.sub.3,R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl which can be interrupted by oxygen or substituted by halogen or cyano, or is C.sub.3 -C.sub.6 alkenyl or C.sub.3 -C.sub.6 alkynyl, or C.sub.3 -C.sub.6 cycloalkyl, has the same meaning as R.sub.2 or is C.sub.1 -C.sub.6 alkoxy, orR.sub.
Type:
Grant
Filed:
July 7, 1980
Date of Patent:
December 21, 1982
Assignee:
Ciba-Geigy Corporation
Inventors:
Georg Pissiotas, Otto Rohr, Haukur Kristinsson
Abstract: A process for protecting cultivated plants against aggressive agricultural chemicals is described in which oxime derivatives of the formula ##STR1## are used as antidotes. Either the cultivated area for the cultivated plants or the cultivated plants themselves or parts of the plant (seeds, tubers, stem parts and the like), as desired, can be treated with these oxime derivatives, which are used as a dressing.
Type:
Grant
Filed:
August 28, 1979
Date of Patent:
August 31, 1982
Assignee:
Ciba-Geigy Corporation
Inventors:
Alfons Lukaszczyk, Henry Martin, Peter J. Diel, Werner Fory, Karl Gatzi, Haukur Kristinsson, Beat Muller, Rene Muntwyler, Johannes P. Pachlatko, Hermann Rempfler, Rolf Schurter, Henry Szczepanski
Abstract: Sensitizers for photoconductive compositions and elements are disclosed. The sensitizers are 2,4,6 tri substituted pyrylium dye salts wherein at least one of said substituents is a 5 or 6 membered heterocyclic ring having at least one atom selected from the group consisting of N, O and S.
Type:
Grant
Filed:
April 26, 1979
Date of Patent:
July 27, 1982
Assignee:
Eastman Kodak Company
Inventors:
Michael T. Regan, George A. Reynolds, Donald P. Specht, James A. VanAllan
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: 4-(((Heterocyclo)thio)methyl)benzoic acids, esters, amides and pharmaceutically-acceptable salts thereof having hypoglycemic activity in mammals, including a method of use and pharmaceutically-acceptable compositions.
Abstract: An 1,3,4-thiadiazole-5-thiol ester of the formula, ##STR1## wherein R is a hydrogen atom or a methyl group, a process for their preparation and a process for preparing a cephalosporin compound of the formula, ##STR2## wherein R is the same as defined above, using the above described 1,3,4-thiadiazole-5-thiol ester.
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
Abstract: Heterocyclic sulfenamides, such as N-[2-chloro-5-(trifluoromethyl)phenyl]-N-[2,4-dinitro-6-trifluoromethyl)ph enyl]-3-nitro-2-pyridinesulfenamide, are useful as miticides, insecticides, fungicides and ovicides.
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: 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: 1,3,4-thiadiazole-2-carboxylic acid derivatives of the formula ##STR1## wherein R is C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkinyl or C.sub.3 -C.sub.6 -cycloalkyl,R.sub.1 is C.sub.1 -C.sub.6 -alkoxycarbonyl, aminocarbonyl, C.sub.1 -C.sub.8 -alkylaminocarbonyl, C.sub.3 -C.sub.6 -cycloalkylaminocarbonyl, di-C.sub.1 -C.sub.8 alkylaminocarbonyl, cyclohexylmethylaminocarbonyl, alkoxyalkylaminocarbonyl, morpholinocarbonyl, pyrrolidinocarbonyl, piperidinocarbonyl or cyano,and n is 0.1 or 2.The compounds wherein n is 1 or 2 have both a high fungicidal and nematocidal activity. The compounds in which n is 0 are the starting products or intermediate products in making the compound in which a sulfonyl or sulfinyl group is present (n=1 or 2) but have also nematocidal properties of their own. All compounds of the invention avoid the undesirable environmental properties and other shortcomings of the prior art products, particularly those of the broadly used mercury compounds.
Type:
Grant
Filed:
December 6, 1979
Date of Patent:
July 28, 1981
Assignee:
Schering Aktiengesellschaft
Inventors:
Ludwig Nusslein, Dietrich Baumert, Ernst A. Pieroh
Abstract: Novel biocidal compounds having the general structural formula ##STR1## wherein R is selected from the group consisting of C.sub.1 --C.sub.4 alkyl, including methyl, ethyl, propyl and butyl, ##STR2## phenyl, substituted phenyl wherein the substituents are selected from the group comprising --CH.sub.3, --CF.sub.3, --NO.sub.2, bromine and chlorine.
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: 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 5, 1979
Date of Patent:
May 5, 1981
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Graham J. Durant, Rodney C. Young, Zev Tashma
Abstract: An 1,3,4-thiadiazole-5-thiol ester of the formula, ##STR1## wherein R is a hydrogen atom or a methyl group, a process for their preparation and a process for preparing a cephalosporin compound of the formula, ##STR2## wherein R is the same as defined above, using the above described 1,3,4-thiadiazole-5-thiol ester.
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
Abstract: Fluorinated-alkyl sulfides represented by [R.sub.f (CH.sub.2).sub.n S].sub.z Q where R.sub.f is fluoroalkyl, n is 2 or 3, z is 1 or 2, and Q is an aryl, alkylaryl, alkyl heterocyclic or heterocyclic radical, are useful as surfactants or as intermediates for the preparation of salt-type, quaternary-salt, or amphoteric surfactants.
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: 2,3-Unsaturated nitrogen-containing heterocyclic compounds with a 3-nitro group and a 2-heterocyclyl alkylamino group. The alkyl group of 2-position substituents is preferably interrupted by sulfur or oxygen. The compounds of the invention are preferably dihydropyrroles or tetrahydropyridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.
Type:
Grant
Filed:
May 30, 1979
Date of Patent:
December 9, 1980
Assignee:
Smith Kline & 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 with alkyl group interrupted by sulfur or oxygen. The 4- and 5-positions of the pyrrole ring can also be substituted.
Type:
Grant
Filed:
May 30, 1979
Date of Patent:
December 9, 1980
Assignee:
Smith Kline & French Laboratories Limited
Abstract: New 4-hydroxy-3-(substitutedmethyl)benzeneacetic acids have been prepared which are useful as starting materials in the preparation of cephalosporin and penicillin derivatives.
Abstract: Useful intermediates for preparing a 1-dethia-1-oxacephalosporin and represented by the following formula: ##STR1## (wherein R is a monovalent group resulting from the elimination of the carbonyl function of an acyl group derived from a carboxylic or carbonic acid;COB is carboxy or protected carboxy; andX is hydrogen or a nucleophilic group)are prepared from the corresponding penicillin 1-oxides of the following formula: ##STR2## (wherein R, COB, and X are as defined above) by heating, if required in the presence of the desulfurizing reagent, or by exchanging the X group with another one under the condition of an appropriate nucleophilic substitution.
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:
August 1, 1978
Date of Patent:
September 2, 1980
Assignee:
Smith Kline & French Laboratories Limited
Inventors:
Graham J. Durant, John C. Emmett, Charon R. Ganellin, Hunter D. Prain
Abstract: Bisamidines carrying one unsaturated nitrogen heterocycle-containing substituent, representative of which is 1-[N'-(2-(5-methyl-4-imidazolyl)methylthio)ethyl)guanidino]-8-[N'-methyl-g uanidino]octane, are histamine H.sub.2 -antagonists.
Type:
Grant
Filed:
May 2, 1978
Date of Patent:
July 15, 1980
Assignee:
Smith Kline & French Laboratories Limited
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