1,3,4-thiadiazoles (including Hydrogenated) Patents (Class 548/136)
  • 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: 4401817
    Abstract: Certain carbonyl-substituted-1-sulfonylbenzimidazole compounds are useful as antiviral agents.
    Type: Grant
    Filed: April 21, 1982
    Date of Patent: August 30, 1983
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Paget, James W. Chamberlin, James H. Wikel
  • Patent number: 4400509
    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
  • 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: 4389403
    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
  • Patent number: 4388464
    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
  • Patent number: 4388319
    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
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4385181
    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
  • Patent number: 4378357
    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.
    Type: Grant
    Filed: December 16, 1977
    Date of Patent: March 29, 1983
    Assignee: Rohm and Haas Company
    Inventors: George A. Miller, Lendon N. Pridgen
  • 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: 4372963
    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
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4372953
    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.
    Type: Grant
    Filed: February 27, 1981
    Date of Patent: February 8, 1983
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Minoru Uchida, Takao Nishi, Kazuyuki Nakagawa
  • Patent number: 4369185
    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
  • Patent number: 4364769
    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
  • Patent number: 4347372
    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
  • Patent number: 4341894
    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
  • Patent number: 4338329
    Abstract: Certain carbonyl-substituted-1-sulfonylbenzimidazole compounds are useful as antiviral agents.
    Type: Grant
    Filed: April 20, 1981
    Date of Patent: July 6, 1982
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Paget, James W., both of Chamberlin, James H. Wikel
  • Patent number: 4338328
    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
    Inventor: George R. White
  • Patent number: 4331668
    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
    Inventors: Michael L. Roantree, Rodney C. Young
  • Patent number: 4325959
    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.
    Type: Grant
    Filed: August 9, 1979
    Date of Patent: April 20, 1982
    Assignee: The Dow Chemical Company
    Inventor: Donald P. Matthews
  • Patent number: 4316021
    Abstract: Certain 1-sulfonyl-2,5(6)-substituted-benzimidazole compounds are useful as antiviral agents.
    Type: Grant
    Filed: September 2, 1980
    Date of Patent: February 16, 1982
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Paget, James H. Wikel
  • Patent number: 4314059
    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.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: February 2, 1982
    Inventors: Chisei Shibuya, Kunihiko Ishii, Takumi Sano, Torao Ishida
  • 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: 4298613
    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.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: November 3, 1981
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Gerald E. Lepone
  • 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: 4282234
    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
  • Patent number: 4281121
    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
  • Patent number: 4269846
    Abstract: New benzoheterocyclic oxadiazolones and triazolones are described. These compounds are useful as anti-allergic reagents.
    Type: Grant
    Filed: October 29, 1979
    Date of Patent: May 26, 1981
    Assignee: USV Pharmaceutical Corporation
    Inventors: Fu C. Huang, John H. Musser
  • Patent number: 4269984
    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.
    Type: Grant
    Filed: July 25, 1980
    Date of Patent: May 26, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Raymond A. Felix
  • Patent number: 4267338
    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
  • Patent number: 4265896
    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
  • Patent number: 4258195
    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.
    Type: Grant
    Filed: March 8, 1979
    Date of Patent: March 24, 1981
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Chisei Shibuya, Kunihiko Ishii, Takumi Sano, Torao Ishida
  • 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: 4254266
    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.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: March 3, 1981
    Assignee: Pennwalt Corporation
    Inventors: Sameeh S. Toukan, Murray Hauptschein
  • Patent number: 4252960
    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.
    Type: Grant
    Filed: February 21, 1980
    Date of Patent: February 24, 1981
    Assignee: PPG Industries, Inc.
    Inventor: Jerome M. Lavanish
  • Patent number: 4238493
    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
    Inventors: Michael L. Roantree, Rodney C. Young
  • Patent number: 4238494
    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
    Inventors: Michael L. Roantree, Rodney C. Young
  • Patent number: 4230865
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-thioureas and ureas which are inhibitors of histamine activity.
    Type: Grant
    Filed: September 8, 1978
    Date of Patent: October 28, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Ganellin
  • Patent number: 4229363
    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.
    Type: Grant
    Filed: September 7, 1978
    Date of Patent: October 21, 1980
    Assignee: Yeda Research and Development Co., Ltd.
    Inventors: Abraham Nudelman, Abraham Patchornik
  • Patent number: 4228291
    Abstract: The compounds are substituted thioalkyl-, aminoalkyl- and oxyalkyl-guanidines which are inhibitors of histamine activity.
    Type: Grant
    Filed: October 4, 1978
    Date of Patent: October 14, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, John C. Emmett, Charon R. Genellin
  • Patent number: 4220766
    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.
    Type: Grant
    Filed: January 10, 1978
    Date of Patent: September 2, 1980
    Assignee: Shionogi & Co., Ltd.
    Inventors: Teruji Tsuji, Mitsuru Yoshioka, Shoichiro Uyeo, Yoshio Hamashima, Ikuo Kikkawa, Wataru Nagata
  • Patent number: 4220652
    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
  • Patent number: 4212875
    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
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4196125
    Abstract: Certain 1-sulfonyl-2,5(6)-substituted-benzimidazole compounds are useful as antiviral agents.
    Type: Grant
    Filed: March 16, 1978
    Date of Patent: April 1, 1980
    Assignee: Eli Lilly and Company
    Inventors: Charles J. Paget, James H. Wikel
  • Patent number: 4191769
    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