Nitrogen Or Chalcogen Attached Indirectly To The Thiazole Ring By Nonionic Bonding Patents (Class 548/214)
  • Patent number: 4288437
    Abstract: Compounds of the formula ##STR1## wherein Ar is phenyl; mono- or di-substituted phenyl, where the substituents are one to two halogens, one to two alkyls of 1 to 3 carbon atoms, or one amino, nitro, cyano or trifluoromethyl; or pyridinyl;R is hydrogen, chlorine, methyl or methoxy;R.sub.1 is hydrogen or methyl;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, methyl-(cycloalkyl of 3 to 8 carbon atoms) or --A--R.sub.4,where A is alkylene of 2 to 3 carbon atoms, and R.sub.4 is hydroxyl, methylamino, dimethylamino, N-methyl-ethylamino, diethylamino, pyrrolidino, piperidino, hexamethyleneimino, morpholino or 4-methyl-1-piperazinyl; orR.sub.1 and R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: September 8, 1981
    Assignee: Boehringer Ingelheim GmbH
    Inventors: Wolfhard Engel, Gunter Trummlitz, Ernst Seeger, Joachim Kahling
  • Patent number: 4285952
    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'-methylgu anidino]octane, are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: November 13, 1979
    Date of Patent: August 25, 1981
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Peter D. Miles
  • Patent number: 4284781
    Abstract: Vanadia supported on a silica-alumina or gamma-alumina support in an amount to provide a vanadia to support weight ratio ranging from about 0.3:1 to about 3:1 substantially entirely within the pores of the support, the vanadia having been placed in molten form substantially within the pores of a support having a surface area greater than about 50 m.sup.2 gram, a porosity greater than about 0.4 cc/gram which further includes an alkali metal, with the vanadium metal to alkali metal mole ratio being from 2:1 to 30:1. At least a portion of the alkali metal is preferably in the form of alkali metal vanadate. The catalyst is used for the production of nitriles from a compound containing at least one alkyl group.
    Type: Grant
    Filed: March 2, 1978
    Date of Patent: August 18, 1981
    Assignee: The Lummus Company
    Inventor: Morgan C. Sze
  • Patent number: 4284632
    Abstract: New 3-cyclicaminoalkoxy-4-phenyl-3-pyrrolin-2-ones are disclosed. These compounds exhibit anti-hypertensive and vasodilatory action.
    Type: Grant
    Filed: September 14, 1979
    Date of Patent: August 18, 1981
    Assignee: Warner-Lambert Company
    Inventors: Gerhard Satzinger, Manfred F. Herrmann, Gustav Hechtfischer
  • Patent number: 4282028
    Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are alkyl or halo; R.sup.3 is hydrogen or alkyl; Z is halo; and R.sup.4 is alkoxycarbonyl, alkoxy, phenyl, substituted phenyl,a group of the formula ##STR2## wherein R.sup.5 and R.sup.6 are hydrogen, alkyl, alkenyl or alkynyl; a group of the formula ##STR3## wherein R.sup.7 and R.sup.8 are hydrogen and alkyl; a five or six-membered aromatic heterocyclic ring of the formula ##STR4## wherein at least one of V, W, X or Y is an oxygen, sulfur or nitrogen atom, R.sup.9 is alkyl and n is 0, 1, 2 or 3 have herbicidal and plant-growth-regulating activity.
    Type: Grant
    Filed: July 25, 1979
    Date of Patent: August 4, 1981
    Assignee: Chevron Research Company
    Inventor: Stephen D. Ziman
  • 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: 4281136
    Abstract: This disclosure relates to a novel class of 2-alkyl-3-haloisothiazolium salts. These salts have been found to be useful in controlling the growth of bacteria and fungi. They have also been found to be useful intermediates in the preparation of novel and known antibacterial and antifungal compounds.
    Type: Grant
    Filed: October 16, 1978
    Date of Patent: July 28, 1981
    Assignee: Givaudan Corporation
    Inventors: Joseph A. Virgilio, Milton Manowitz, Emanuel Heilweil
  • Patent number: 4279902
    Abstract: Acetamide derivatives are provided having the structure ##STR1## wherein X is a single bond, --CH.sub.2 -- or --O--, R.sup.1 and R.sup.2 may be the same or different and are lower alkyl, phenyl-lower alkoxy-lower alkyl, lower alkenyl, phenyl-lower alkyl or lower alkoxy, or ##STR2## may be taken together to form a 5- to 7-membered heterocyclic ring optionally containing one other hetero atom, such as nitrogen, sulfur or oxygen; Y is hydroxyl, OR wherein R is lower alkyl, lower alkenyl or lower alkanoyl, or ##STR3## wherein R.sup.1 and R.sup.2, and R.sup.1 and R.sup.2 taken together with the nitrogen to which they are attached are as defined above, and n is 1 to 6.These compounds are useful as anti-arrhythmia agents and have been found to be effective in the treatment of acute myocardial infarction.
    Type: Grant
    Filed: August 6, 1980
    Date of Patent: July 21, 1981
    Assignee: E. R. Squibb & Sons, Inc.
    Inventors: Frederic P. Hauck, Glenn A. Jacobs
  • Patent number: 4279904
    Abstract: Novel 3-amino-1-benzoxepine derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.7 R.sub.8 ;R.sub.7 and R.sub.8 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.7 and R.sub.8 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or nitrogen, orR.sub.1 and R.sub.2 are together a 5 to 7 member ring or said ring having heterogeneous oxygen, sulfur or NR.sub.9 ;R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: July 21, 1981
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann, Henning Heinemann
  • Patent number: 4279905
    Abstract: Novel, 3-amino-1-benzoxepin-5 (2H)-one derivatives and methods for their production are disclosed. These derivatives correspond to the Formula I: ##STR1## wherein: R.sub.1 and R.sub.2 independently of one another arehydrogen,C.sub.1 -C.sub.5 alkyl,C.sub.1 -C.sub.5 alkyl substituted with a terminal phenyl, or a phenyl containing one or two halogens, methyl or methoxy groups, a 3,4-methylenedioxy or a 3,4-ethylenedioxy group,C.sub.2 -C.sub.5 alkyl substituted with terminal hydroxy or methoxy or,C.sub.3 -C.sub.4 alkenyl; orone of R.sub.1 and R.sub.2 are hydrogen or a C.sub.1 -C.sub.5 alkyl and the other is a C.sub.2 -C.sub.5 alkyl substituted with a terminal NR.sub.5 R.sub.6 ;R.sub.5 and R.sub.6 independently of one another are hydrogen or C.sub.1 -C.sub.5 alkyl; orR.sub.5 and R.sub.6 are together a 5 to 7 member ring, orR.sub.5 and R.sub.6 are together a 5 to 7 member ring having heterogeneous oxygen, sulfur or nitrogen;R.sub.1 and R.sub.2 are together a 5 to 7 member ring, orR.sub.1 and R.sub.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: July 21, 1981
    Assignee: Kali-Chemie Pharma GmbH
    Inventors: Heinrich-Wilhelm Ohlendorf, Klaus-Ullrich Wolf, Wilhelm Kaupmann
  • Patent number: 4279911
    Abstract: The invention relates to compounds of the general formula (I) ##STR1## and physiologically acceptable salts, N-oxides, hydrates and bioprecursors thereof, in which Y represents .dbd.O, .dbd.S, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 represents hydrogen, nitro, cyano, lower alkyl, aryl, lower alkylsulphonyl or arylsulphonyl; R.sub.1 and R.sub.2, which may be the same or different, each represent hydrogen lower alkyl, cycloalkyl, lower alkenyl, aralkyl, hydroxy, lower trifluoroalkyl, lower alkyl substituted by hydroxy, lower alkoxy, amine, lower alkylamino or dialkylamino, or R.sub.1 and R.sub.2 together with the nitrogen atom to which they are attached form a 5 to 7 membered heterocyclic ring which may contain other heteroatoms or the group ##STR2## where R.sub.
    Type: Grant
    Filed: June 6, 1980
    Date of Patent: July 21, 1981
    Assignee: Glaxo Group Limited
    Inventors: Michael Martin-Smith, Barry J. Price, John Bradshaw, John W. Clitherow
  • Patent number: 4268676
    Abstract: Compounds of the formula, I, ##STR1## wherein: Y is hydrogen or lower alkyl; and X is a thiazolamino radical, a furfurylamino radical or a radical of the formula, ##STR2## in which R, R.sup.1, and R.sup.2 are the same or different and selected from the group consisting of hydrogen and lower alkyl, and R.sup.3 is selected from the group consisting of lower alkenyl, halo-lower alkenyl, lower alkynyl, lower akloxycarbonyl, thienyl, formamyl, tetrahydrofuryl and benzene sulfonamide.Also disclosed are novel methods for treatment of neoplastic disease states in animals, which methods comprise administering a therapeutically effective amount of a compound of the formula, Ia, ##STR3## wherein: Y is hydrogen or lower alkyl; and Z is a thiazolamino radical, a furfurylamino radical, a cyclpropylamino radical, a pyridylamino radical, or a radical of the formula, ##STR4## in which R.sup.4, R .sup.5, and R.sup.6 are the same or different and selected from the group consisting of hydrogen and lower alkyl, and R.sup.
    Type: Grant
    Filed: December 5, 1979
    Date of Patent: May 19, 1981
    Assignee: University Patents, Inc.
    Inventor: William A. Remers
  • Patent number: 4267341
    Abstract: 2,3-Substituted-1,2-isothiazolium salts have antibacterial and antifungal activity and are useful in agriculture against diseases and decay of fruits and vegetables, as well as a slimicide in industry.
    Type: Grant
    Filed: February 8, 1979
    Date of Patent: May 12, 1981
    Assignee: Merck & Co., Inc.
    Inventors: Joshua Rokach, Clarence S. Rooney, Edward J. Cragoe, Jr.
  • 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: 4256752
    Abstract: There are prepared compounds corresponding to the formula ##STR1## in which X is a 5-membered or 6-membered aromatic heterocyclic radical which is attached through a carbon atom to the adjacent CH.sub.2 -group and which contains from 1 to 3 nitrogen atoms or one nitrogen atom and one oxygen or sulphur atom, and which may be substituted once or twice by substituents defined hereinbelow, each R.sup.1 represents hydrogen or a C.sub.1 -C.sub.4 -alkyl group, Alk represents a C.sub.2 -C.sub.6 -alkylene chain and Ac is defined hereinbelow and their salts.
    Type: Grant
    Filed: February 13, 1979
    Date of Patent: March 17, 1981
    Assignee: Deutsche Gold- und Silber-Scheideanstalt vormals Roessler
    Inventors: Walter von Bebenburg, Norbert Schulmeyer, Istvan Szelenyi
  • Patent number: 4255428
    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
  • 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: 4252739
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yields. The process involves reacting an alkylating agent and an activated methylene compound in the presence of an onium compound, an alkali metal compound and water, which while only necessary in trace amounts can be present in substantial quantities.
    Type: Grant
    Filed: August 20, 1979
    Date of Patent: February 24, 1981
    Assignee: Emery Industries, Inc.
    Inventors: Richard G. Fayter, Jr., John F. White, Eugene G. Harris
  • 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: 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: 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: 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: 4225711
    Abstract: This invention relates to compositions of matter classified in the art of chemistry as substituted 2-[(methylsulfinyl)acetyl]-3-heterocyclicindoles, various derivatives thereof, and to the processes for making and using such compositions as immunosuppressants.
    Type: Grant
    Filed: October 2, 1978
    Date of Patent: September 30, 1980
    Assignee: Schering Corporation
    Inventors: Martin Steinman, Pirouz Tahbaz
  • Patent number: 4221584
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 is alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo, R.sup.2, R.sup.3 and R.sup.4 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, haloalkyl of 1 to 2 carbon atoms and 1 to 3 of the same or different halogens selected from fluoro, chloro, bromo or iodo, nitro, hydroxy, alkoxyalkyl of 2 to 6 carbon atoms, fluoro, bromo, chloro or iodo; R.sup.5 and R.sup.
    Type: Grant
    Filed: February 9, 1979
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Stephen D. Ziman
  • Patent number: 4210658
    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
  • Patent number: 4204065
    Abstract: Soft quaternary surface active agents having the formula: ##STR1## wherein >N represents a tertiary open chain or cyclic aliphatic amine; wherein >N represents an unsaturated amine; wherein R represents a member selected from the group consisting of a hydrogen atom, a C.sub.1 -C.sub.20 open chain or cyclo alkyl group, a C.sub.1 -C.sub.20 alkoxyalkyl group, a C.sub.1 -C.sub.20 acyloxyalkyl group, a C.sub.1 -C.sub.20 haloalkyl group, a C.sub.1 -C.sub.20 carboxyalkyl group, an aryl group, and a substituted aryl group, whose substituents are selected from the group consisting of a halogen atom, an O--C.sub.1 -C.sub.4 alkyl group, an O--C.sub.1 -C.sub.8 acyl group, a nitro group, a carboxyl group, and a carboethoxy group; wherein R.sub.1 represents a C.sub.9 -C.sub.22 straight or branched alkyl group, a --(CH.sub.2).sub.n -- ##STR2## group, wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are each selected from the group consisting of a hydrogen atom, a methyl group or an ethyl group, a C.sub.0 -C.sub.
    Type: Grant
    Filed: December 13, 1978
    Date of Patent: May 20, 1980
    Assignee: Interx Research Corporation
    Inventor: Nicolae S. Bodor
  • Patent number: 4197305
    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-(nitrometylene 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)ethyl)isothiour eido]propane. The compounds of this invention are inhibitors of H-2 histamine receptors.
    Type: Grant
    Filed: September 11, 1978
    Date of Patent: April 8, 1980
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin
  • Patent number: 4196126
    Abstract: Disclosed are 3-methyl-5-isothiazolyl-3-alkoxyureas, such as 1-(3-methyl-5-isothiazolyl)-3-methoxy-3-methylurea, and the method of controlling broadleaf and grassy weeds, such as Echinochloa crusgalli (L.) Beauv. (barnyardgrass), with these ureas.
    Type: Grant
    Filed: November 4, 1977
    Date of Patent: April 1, 1980
    Assignee: PPG Industries, Inc.
    Inventor: Dennis K. Krass
  • 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
  • Patent number: 4189434
    Abstract: New and valuable polycyclic compounds which contain nitrogen-containing rings and have a strong action on plants, agents for influencing plant growth containing these compounds, and a method of influencing plant growth with these compounds.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: February 19, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Platz, Werner Fuchs, Norbert Rieber, Ulf-Rainer Samel, Johann Jung, Bruno Wuerzer
  • Patent number: 4183856
    Abstract: Urea derivatives of the formula ##STR1## (wherein Ar represents a residue of 5- or 6-membered heteroaromatic ring; R represents a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sup.1 represents a C.sub.1 -C.sub.6 alkyl group; and R.sup.2 represents a C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or C.sub.1 -C.sub.6 alkoxy group) are produced by reacting an amine of the formulaAr--NH--R(wherein Ar and R have the significance given above) with a carbamoyl halogenide of the formula ##STR2## (wherein X represents a halogen atom, and R.sup.1 and R.sup.2 have the significance given above) in the presence of a Lewis acid in an inert solvent.
    Type: Grant
    Filed: April 10, 1978
    Date of Patent: January 15, 1980
    Assignee: Shionogi & Co., Ltd.
    Inventors: Yasuo Makisumi, Takashi Sasatani, Akira Murabayashi
  • Patent number: 4173644
    Abstract: The compounds are dithiocarbamates and isothioureas which are histamine H.sub.2 -antagonists. Two compounds of the invention are 2-(5-methyl-4-imidazolylmethylthio)ethyl N-methyldithiocarbamate and S-[2-(5-methyl-4-imidazolyl-methylthio)ethyl]-N-cyano-N'-methylisothiourea .
    Type: Grant
    Filed: July 28, 1978
    Date of Patent: November 6, 1979
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Thomas H. Brown, Graham J. Durant, Charon R. Ganellin, Robert J. Ife
  • Patent number: 4166857
    Abstract: The compounds are 1-amino-2-heterocyclic-alkylamino-cyclobut-1-ene-3,4-diones which are histamine H.sub.2 -antagonists.
    Type: Grant
    Filed: July 27, 1978
    Date of Patent: September 4, 1979
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Charon R. Ganellin, Rodney C. Young
  • Patent number: 4166856
    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: March 31, 1978
    Date of Patent: September 4, 1979
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Graham J. Durant, Charon R. Ganellin, Geoffrey R. Owen, Rodney C. Young