Nitrogen Attached Directly To The Thiazole Ring By Nonionic Bonding Patents (Class 548/184)
  • Patent number: 4863947
    Abstract: This invention relates to novel N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.
    Type: Grant
    Filed: August 11, 1986
    Date of Patent: September 5, 1989
    Assignee: Rohm and Haas
    Inventor: Richard M. Jacobson
  • Patent number: 4863945
    Abstract: Pyrrolobenzimidazoles of the formula: ##STR1## are useful for treatment of heart and circulatory diseases. R.sub.1 is substituted phenyl; or optionally substituted naphthyl or a five- or six-membered heterocyclic group which can be condensed with a phenyl ring to form a bicyclic radical. R.sub.2 is hydrogen, alkyl, alkenyl or cycloalkenyl; R.sub.3 is alkyl, alkenyl or hydroxyalkyl or with R.sub.2 together forms cycloakylene; or R.sub.2 and R.sub.3 together form alkylidene or cycloalkylidene. R.sub.4 is hydrogen or lower alkanoyl. X is a valency bond, alkylene, vinylene, imino or carbonylamino. T stands for two hydrogen atoms. When X is a valency bond, R.sub.1 can also be hydrogen, hydrocarbyl which may also contain oxygen, amino, sulfur, carbonyl and sulfonyl groups. When X is imino or carbonylamino or when R.sub.1 is a bicyclic radical, T can also be oxygen. The compounds also include the tautomers and physiologically acceptable salts with inorganic and organic acids.
    Type: Grant
    Filed: December 10, 1987
    Date of Patent: September 5, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Walter-Gunar Friebe, Alfred Mertens, Klaus Strein, Erwin Boehm
  • Patent number: 4851422
    Abstract: The compound represented by the formula: ##STR1## where R.sup.1 stands for amino or an organic residue bonded through nitrogen; R.sup.2 stands for carboxyl or a group derivable therefrom; R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently stand for hydrogen or an organic residue, including the case where R.sup.5 or R.sup.6 forms a chemical bond or a ring with R.sup.7 or R.sup.8 ; X stands for hydrogen, methoxy or formylamino; or a salt thereof, produceable by the present method, exhibits excellent antimicrobial activity, and is utilized as antimicrobial agents.
    Type: Grant
    Filed: April 30, 1986
    Date of Patent: July 25, 1989
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideaki Natsugari, Yasuhiko Kawano, Akira Morimoto, Kouichi Yoshioka
  • Patent number: 4826990
    Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## Y is ##STR3## Z is ##STR4## R.sup.1 is ##STR5## n is 0-5; R.sup.2 is hydrogen, loweralkyl, loweralkoxy, lower alkoxycarbonyl, trifluoromethyl, nitro, cyano or halo;R.sup.3 is ##STR6## W represents a bond or ##STR7## m is 1-15; R.sup.4 is hydrogen or loweralkyl;R.sup.5 is lower alkyl, monofluoroloweralkyl, difluoroloweralkyl, polyfluoroloweralkyl, perfluoroloweralkyl or ##STR8## R.sup.6 is hydrogen, lower alkyl, ##STR9## and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and as antiinflammatory agents.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: May 2, 1989
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Reinhold H. W. Bender, Anthony F. Kreft, III
  • Patent number: 4808210
    Abstract: A 5-pyrazolone of the formula ##STR1## wherein R is selected from the group consisting of mono- and polycyclic aromatic of 6 to 14 carbon atoms, heterocyclic optionally substituted with phenyl, ##STR2## and benzyl, all optionally substituted with at least one member of the group consisting of fluorine, chlorine, bromine, --CF.sub.3, optionally unsaturated alkyl of 1 to 8 carbon atoms and the radical OZ in which Z is an optionally unsaturated alkyl of 1 to 8 carbon atoms or an acyl of a carboxylic acid of 1 to 6 carbon atoms, A is selected from the group consisting of halogen, --CF.sub.3 and --CN, B and C are individually selected from the group consisting of hydrogen, halogen, --OH, --OR' and R' is optionally unsaturated alkyl of 1 to 8 carbon atoms, acyl of 1 to 6 carbon atoms, alkyl sulfonyl of 1 to 8 carbon atoms, aryl sulfonyl of 6 to 18 carbon atoms and benzyl optionally substituted with a member of the group consisting of fluorine, chlorine, bromine, --CF.sub.
    Type: Grant
    Filed: September 11, 1987
    Date of Patent: February 28, 1989
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Pierre Girault
  • Patent number: 4798893
    Abstract: A method for the synthesis of the 2-propanone (I) is described starting from alkoxide (II) through the lactone (IV). ##STR1## Excellent control of the location of the substitution on the phenyl ring is achieved and the reaction proceeds in high yield.
    Type: Grant
    Filed: September 21, 1987
    Date of Patent: January 17, 1989
    Assignee: McNeilab, Inc.
    Inventors: David A. Cherry, Cynthia A. Maryanoff, John E. Mills, Roy A. Olofson, James D. Rodgers
  • Patent number: 4795755
    Abstract: This invention relates to heterocyclic 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, 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 2-6 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.
    Type: Grant
    Filed: March 1, 1982
    Date of Patent: January 3, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4792606
    Abstract: A process for the preparation of a dimeric aromatic acyl cyanide of the formula ##STR1## in which Ar is optionally substituted phenyl, naphthyl or hetaryl,comprising reaction an acyl halide of the formulaAr--CO--Halin whichHal is fluorine, chlorine or bromine, with an alkali metal cyanide in a two-phase system comprising water and a water-immiscible or only sparingly water-miscible aliphatic ketone, and in the presence of a phase-transfer catalyst. The products are known intermediates for pesticides.
    Type: Grant
    Filed: July 16, 1987
    Date of Patent: December 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Hermann-Dieter Krall
  • Patent number: 4782083
    Abstract: Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein: one of R.sub.1 and R.sub.2 is hydrogen or C.sub.1-4 alkyl and the other is C.sub.1-4 alkyl or R.sub.1 and R.sub.2 together are C.sub.2-5 -polymethylene;either R.sub.3 is hydrogen, hydroxy, C.sub.1-6 alkoxy or C.sub.1-7 acyloxy and R.sub.4 is hydrogen or R.sub.3 and R.sub.4 together are a bond;R.sub.5 is hydrogen C.sub.1-6 alkyl optionally substituted by halogen hydroxy, C.sub.1-6 alkoxy, C.sub.1-6 alkoxycarbonyl, carboxy or amino optionally substituted by one or two independent C.sub.1-6 alkyl groups, or C.sub.2-6 alkenyl, amino optionally substituted by a C.sub.1-6 alkyl or C.sub.1-6 alkenyl group or by a C.sub.1-6 alkanoyl group optionally substituted by up to three halo atoms, by a phenyl group optionally substituted by C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or aryl or hetroaryl, either being optionally substituted by one or more groups or atoms selected from the class of C.sub.1-6 alkyl, C.sub.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: November 1, 1988
    Assignee: Beecham Group P.L.C.
    Inventors: Frederick Cassidy, Geoffrey Stemp, John M. Evans
  • Patent number: 4775677
    Abstract: The present invention provides novel [3-substituted-2-(substituted imino)-4-oxo-5-thiazolidinylidene]acetic acids, and novel pharmaceutical compositions and methods of use thereof. The novel acids of the invention are leukotriene antagonists having activity useful for treating asthma, allergies, cardiovascular diseases, migraines, and inflammation.
    Type: Grant
    Filed: January 6, 1987
    Date of Patent: October 4, 1988
    Assignee: Warner-Lambert Company
    Inventors: David T. Connor, Roderick J. Sorenson
  • Patent number: 4762848
    Abstract: Heterocyclic sulfides of the general formula heterocycle-S-R, a process for their preparation and, in particular, their use for immunostimulation, immunorestoration and cytostatic treatment, and pharmaceutical agents, which contain a sulfide of this type, for these indications.
    Type: Grant
    Filed: March 10, 1986
    Date of Patent: August 9, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Karl-Heinz Scheunemann, Walter Durckheimer, Jurgen Blumbach, Michael Limbert, Hans-Ulrich Schorlemmer, Gerhard Dickneite, Hans-Harald Sedlacek
  • Patent number: 4762932
    Abstract: Compounds useful for inhibiting gastric acid secretion and for the treatment of peptic ulcers caused or exacerbated by gastric acidity having the following formula (I): ##STR1## in which R.sup.1 and R.sup.2, are H, C.sub.1-10 alkyl, C.sub.3-8 cycloalkyl or cycloalkylalkyl in which the alkyl part is C.sub.1-6 and the cycloalkyl part is C.sub.3-8, each of the alkyl, cycloalkyl and cycloalkylalkyls being optionally substituted by one or more halogens selected from F, Cl and Br, provided that at least one of R.sup.1 and R.sup.2 is a halogen substituted alkyl, cycloalkyl or cycloalkylalkyl and provided that there is no halogen substituent on the carbon directly attached to the nitrogen; and X, m, Y, n and R.sup.3 are as described in the specification; and the pharmaceutically-acceptable acid-addition salts thereof.
    Type: Grant
    Filed: June 2, 1986
    Date of Patent: August 9, 1988
    Assignees: Imperial Chemical Industries, Ltd., ICI Americas, Inc.
    Inventors: Tobias O. Yellin, Philip N. Edwards, Michael S. Large
  • Patent number: 4746669
    Abstract: Thiazole derivatives have been made, for example, by reacting a 2-aryl-2,2-dialkoxyethylamine with an appropriately substituted aryl acetyl halide followed by treating the resulting amide with diphosphoryl pentasulfide. The thiazole derivatives are found to be effective immunoregulants.
    Type: Grant
    Filed: March 26, 1987
    Date of Patent: May 24, 1988
    Assignee: Merck & Co., Inc.
    Inventors: Charles G. Caldwell, Ihor Kopka, Milton L. Hammond, Robert A. Zambias
  • Patent number: 4742060
    Abstract: Novel insecticides of the formula ##STR1## in which n is 0 or 1,X is S, O, ##STR2## Y is N or ##STR3## Z is a 5- or 6-membered nitrogen-containing heterocyclic ring, and R to R.sup.9 variously represent hydrogen or specified organic radicals.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: May 3, 1988
    Assignee: Nihon Tokushu Noyaku Seizo K. K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4740231
    Abstract: 1-Aryl-5-alkoximinoalkylamino-pyrazoles of the formula ##STR1## in which R represents cyano or nitro, or represents an optionally substituted heterocyclic radical,R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen or alkyl, or represents optionally substituted aryl,R.sup.3 represents hydrogen, alkyl or alkenyl, or represents in each case optionally substituted aralkyl or aryl andAr represents optionally substituted phenyl or pyridyl,are active as herbicides and plant growth regulants. Compounds of the formula ##STR2## in which R" has the same definition as R other than cyano, are also active and useful as intermediates as well.
    Type: Grant
    Filed: May 22, 1986
    Date of Patent: April 26, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhold Gehring, Otto Schallner, Jorg Stetter, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
  • Patent number: 4696933
    Abstract: The invention relates to amide 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 is a hydrogen or 1-10C alkyl, 3-8C cycloalkyl, 4-14C cycloalkyl, 3-6C alkenyl, 3-6C alkynyl, 1-6C alkanoyl, 6-10C aryl, 7-11C aralkyl or 7-11C aroyl, the aryl, aralkyl and aroyl radical being optionally substituted; ring X is a heterocyclic ring as defined in the specification; A is phenylene or 5-7C cycloalkylene, or a 1-8C alkylene into which is optionally inserted one or two groups; D is O or S; and R.sup.2 and R.sup.3 are hydrogen or a variety of radicals described in the specification: and the pharmaceutically-acceptable acid-addition salts thereof. Manufacturing processes and pharmaceutical compositions are also described.
    Type: Grant
    Filed: February 12, 1985
    Date of Patent: September 29, 1987
    Assignees: ICI Americas Inc., Imperial Chemical Industries PLC
    Inventors: Tobias O. Yellin, David J. Gilman
  • Patent number: 4697020
    Abstract: Compounds of the class of 2,2'-azines of 2,4-thiazolidinediones which are substituted in at least one of the 3-positions by allyl, 1-methylallyl, 2-methylallyl or 2-propynyl and in at least one of the 5-positions by hydroxy, and may further contain methyl groups in the remaining 3-position and in the 5-positions, and the corresponding tautomeric 1-[[4-oxo-2-thiazolidinylidene]amino]-5-hydroxy-2-thiohydantoins and 5,5'-dihydroxy-2,2'-dithio-1,1'-bihydantoins have valuable pharmacological properties. In particular, they inhibit the growth of tumours, while their toxicity is low in comparison with their tumour-inhibiting effectiveness. A specific embodiment is the 2,2'-azine of 3-(2-methylallyl)-5-methyl-2,4-thiazolidinedione and of 3-methyl-5-hydroxy-2,4-thiazolidinedione.
    Type: Grant
    Filed: October 9, 1986
    Date of Patent: September 29, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Angelo Storni, Alex Meisels
  • Patent number: 4663341
    Abstract: This invention relates to N-aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds which are useful as pesticides, compositions containing those compounds, methods of controlling pests and processes for preparing these compounds.
    Type: Grant
    Filed: January 11, 1985
    Date of Patent: May 5, 1987
    Assignee: Rohm and Haas Company
    Inventor: Richard M. Jacobson
  • Patent number: 4636516
    Abstract: Novel 3,5-di-tert-butyl-4-hydroxyphenyl-substituted heterocyclic compounds shown by the formula ##STR1## wherein .circle.Het -- represents a specific heterocyclic group and the salts thereof.The compounds have an anti-inflammatory, an anti-pyretic, an analgesic, an anti-arthritic, and an immunoregulatory activity. Hence, they are particularly useful as an antirheumatics.
    Type: Grant
    Filed: February 11, 1982
    Date of Patent: January 13, 1987
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Kazuo Kubo, Yasuo Isomura, Shuichi Sakamoto, Hiroshige Homma
  • Patent number: 4629794
    Abstract: A series of novel antibacterially active derivatives of indolmycin as well as some prodrug forms of indolmycin is disclosed. A novel process for the production of these compounds is also disclosed.
    Type: Grant
    Filed: January 23, 1986
    Date of Patent: December 16, 1986
    Assignee: Pfizer Inc.
    Inventor: John P. Dirlam
  • Patent number: 4624962
    Abstract: Compounds of the formula I ##STR1## in which n denotes 0-3,R.sup.1 and R.sup.1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired;R.sup.2 denotes hydrogen, alkyl or alkenyl;R.sup.3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R.sup.2 and R.sup.3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl,R.sup.4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted;R.sup.5 denotes hydrogen or alkyl, hydroxyl or alkoxy andR.
    Type: Grant
    Filed: February 1, 1985
    Date of Patent: November 25, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Rainer Henning, Hansjorg Urbach, Rolf Geiger, Volker Teetz, Bernward Scholkens
  • Patent number: 4612326
    Abstract: Sulfur-containing bis-amino carbamate compounds exhibit outstanding acaricidal, nematocidal and insecticidal activity.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: September 16, 1986
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. D'Silva
  • Patent number: 4609737
    Abstract: Novel 2-guanidinothiazoline compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom, and the acid addition salts thereof; they are important intermediate compounds for preparing famotidine and thiotidine which are medicaments useful as gastric acid secretion inhibitors.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: September 2, 1986
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Yasufumi Hirata, Isao Yanagisawa
  • Patent number: 4584385
    Abstract: A series of novel antibacterially active derivatives of indolmycin as well as some prodrug forms of indolmycin is disclosed. A novel process for the production of these compounds is also disclosed.
    Type: Grant
    Filed: February 4, 1985
    Date of Patent: April 22, 1986
    Assignee: Pfizer Inc.
    Inventor: John P. Dirlam
  • Patent number: 4582842
    Abstract: Novel 6H-dibenz[b,e] [1,4]oxathiepin derivatives of the formula I and Ia are employed in the treatment and control of allergic conditions such as allergic asthma.
    Type: Grant
    Filed: September 26, 1983
    Date of Patent: April 15, 1986
    Assignees: Merck & Co., Inc., Merck Frosst Canada
    Inventors: Edward J. Cragoe, Jr., Clarence S. Rooney
  • Patent number: 4581453
    Abstract: The invention relates to guanidinothiazol derivatives of Formula (I) as defined herein, said compounds being useful for influencing lipid metabolism, as antithombotic agents and as antimycotic agents. Also included in the invention are compositions containing said guanidinothiazol derivatives of Formula (I) and the use of said compounds and compositions for treatment of the above-mentioned conditions. In addition, the invention includes methods for the manufacture of the guanidinothiazole derivatives of Formula (I).
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: April 8, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Ippen, Elisabeth Perzborn, Walter Puls, Klaus Schaller, Friedel Seuter
  • Patent number: 4576965
    Abstract: Pesticidal oxime N-alkyl-N-.alpha.-haloacyl-carbamates represented by the structure: ##STR1## wherein R represents an imino radical, R' and R" represent alkyl radicals and X is chlorine, fluorine or bromine.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: March 18, 1986
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4572912
    Abstract: The compounds of formula (I): ##STR1## [in which: R.sup.1 and R.sup.2 are the same or different and each represents hydrogen or C.sub.1 -C.sub.5 alkyl;R.sup.3 represents hydrogen, an acyl group, a (C.sub.1 -C.sub.6 alkoxy)carbonyl group or an aralkyloxycarbonyl group;R.sup.4 and R.sup.5 are the same or different and each represents hydrogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy, or R.sup.4 and R.sup.5 together represent a C.sub.1 14 C.sub.4 alkylenedioxy group;n is 1, 2 or 3;W represents the --CH.sub.2 --, >CO or >CH--OR.sup.6 group (in which R.sup.6 represents any one of the atoms or groups defined for R.sup.3 and may be the same as or different from R.sup.3); andY and Z are the same or different and each represents oxygen or imino]and pharmaceutically acceptable salts thereof have various valuable therapeutic effects on the blood system and may be prepared by a process which includes reacting a corresponding halopropionic acid derivative with thiourea.
    Type: Grant
    Filed: August 28, 1984
    Date of Patent: February 25, 1986
    Assignee: Sankyo Company Limited
    Inventors: Takao Yoshioka, Eiici Kitazawa, Tomoyuki Kurumada, Mitsuo Yamazaki, Kazou Hasegawa
  • Patent number: 4570000
    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-lOC 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 is 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: July 13, 1984
    Date of Patent: February 11, 1986
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Derrick F. Jones, Keith Oldham
  • Patent number: 4562261
    Abstract: Novel 2-guanidinothiazoline compounds of the general formula ##STR1## wherein R represents a hydrogen atom or a lower alkyl group, and X represents a halogen atom, and the acid addition salts thereof; they are important intermediate compounds for preparing famotidine and thiotidine which are medicaments useful as gastric acid secretion inhibitors.
    Type: Grant
    Filed: April 5, 1984
    Date of Patent: December 31, 1985
    Assignee: Yamanouchi Pharmaceutical Co., Ltd.
    Inventors: Yasufumi Hirata, Isao Yanagisawa
  • Patent number: 4560751
    Abstract: Compounds of the general formula I ##STR1## where R is unsubstituted or substituted alkyl, alkenyl, aryl or hetaryl and R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted alkyl or aryl, or, together with the nitrogen, form a heterocyclic ring, are prepared by a process wherein a compound of the general formula II ##STR2## is reacted with a water-soluble monohaloacetate in an aqueous alkaline medium. They are very useful coupling components for the preparation of azo dyes.
    Type: Grant
    Filed: June 30, 1983
    Date of Patent: December 24, 1985
    Assignee: BASF Aktiengesellschaft
    Inventor: Guenther Seybold
  • Patent number: 4558135
    Abstract: A process for the preparation of dithiazolyl disulfides by the catalytic oxidation of a 2-mercaptothiazole with ammonia and either oxygen or an oxygen-containing gas at a temperature of between 0.degree. and 150.degree. C.
    Type: Grant
    Filed: November 23, 1981
    Date of Patent: December 10, 1985
    Assignee: Akzona Incorporated
    Inventors: Hans-Georg Zengel, Manfred Bergfeld, Ludwig Eisenhuth
  • Patent number: 4551472
    Abstract: Unsymmetrical N-substituted bis-carbamoyl sulfide compounds exhibit exceptional broad spectrum pesticidal activity coupled with extremely low mammalian toxicity and phytotoxicity.
    Type: Grant
    Filed: January 9, 1984
    Date of Patent: November 5, 1985
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva
  • Patent number: 4525477
    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 tetrahydropyrridines or pyrimidines. The compounds of the invention are histamine H.sub.2 -receptor antagonists.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: June 25, 1985
    Assignee: Smith Kline & French Laboratories Limited
    Inventors: Michael L. Roantree, Rodney C. Young
  • Patent number: 4517183
    Abstract: The present invention provides pharmaceutical compositions containing N-substituted aziridine-2-carboxylic acid derivatives of the general formula: ##STR1## wherein X is a carboxyl, a cyano, an alkoxycarbonyl or an optionally substituted carbamoyl radical, R is a hydrogen atom, an aliphatic hydrocarbon radical which is saturated or can contain one or more unsaturations and can be substituted one or more times by halogen, alkoxy, hydroxyl, dialkylamino, dialkylaminoxy, cycloalkylamino, acylamino, acyl, nitro, alkylthio, alkylsulphinyl, alkylsulphonyl, cyano, carboxyl, alkoxycarbonyl or carbamoyl or by cycloalkyl or cycloalkenyl radicals optionally carrying alkyl, alkoxy or alkoxycarbonyl radicals, optionally interrupted by hetero atoms and optionally bridged, or by an aryl, hetaryl, aryloxy, arylthio, acyloxy, alkoxycarbonylamino or isothioureido radical, or R is a cycloalkyl or cycloalkenyl radical optionally substituted by alkyl, alkoxy or oxo groups, optionally interrupted by hetero atoms and optionally bri
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: May 14, 1985
    Assignee: Boehringer Mannheim GmbH
    Inventors: Elmar Bosies, Wolfgang Kampe, Max Thiel, Uwe Bicker, Dietmar Boerner
  • 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: 4465504
    Abstract: An N-(2,2,2-trifluoroethyl)-N-alkyl-azolyloxyacetic acid amides of the formula ##STR1## in which R and R.sup.1 have the meaning given in the description, a process for the production of which is described, find use as herbicides. The intermediate products of the general formulae ##STR2## in which R.sup.1 in each case has the same meaning as in formula (I), for the preparation of the compounds (I) are also new.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: August 14, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Forster, Volker Mues, Bernd Baasner, Hermann Hagemann, Ludwig Eue, Robert Schmidt
  • 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: 4458077
    Abstract: Compounds of the formulaAr--(CH.sub.2).sub.m --X--(CH.sub.2).sub.n --ONHRwherein R is ##STR1## wherein R.sup.1 is hydrogen or lower alkyl;X is O or CH.sub.2 ;m=0 or 1;n=2 or 3; andAr is a moiety selected from the group ##STR2## wherein R.sub.2 is hydrogen or lower alkyl, ##STR3## with the proviso that when Ar is ##STR4## and X is CH.sub.2, then R is other than ##STR5## and the pharmacologically acceptable salts thereof have H.sub.2 -antagonist activity and activity in decreasing gastric acid secretions.
    Type: Grant
    Filed: November 22, 1982
    Date of Patent: July 3, 1984
    Assignee: American Home Products Corporation
    Inventor: John R. Potoski
  • Patent number: 4455295
    Abstract: N-(p-sulfophenyl)-cinnamamide, which is optionally present in the form of a salt, can be prepared by the reaction of cinnamoyl chloride with sulphanilic acid in the presence of a tertiary amine. The new compound can be used in light-protection agents.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: June 19, 1984
    Assignee: Haarmann & Reimer GmbH
    Inventors: Rudolf Hopp, Horst Finkelmeier, Roland Langner
  • Patent number: 4451475
    Abstract: The invention relates to cyclic sulphenamides of Formula I and methods for their manufacture. Also included in the invention are compositions containing said cyclic sulphenamides and methods for the use of said compounds and compositions as lipoxygenase inhibitors.
    Type: Grant
    Filed: April 14, 1982
    Date of Patent: May 29, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf-Dieter Busse, Edmund Krauthausen, Mithat Mardin
  • 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: 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: 4433154
    Abstract: Bis(carboxamide) derivatives being useful as histamine H.sub.2 receptor antagonists or anti-peptic ulcer agents are provided from certain dicarboxylic acid derivatives.
    Type: Grant
    Filed: December 7, 1981
    Date of Patent: February 21, 1984
    Assignee: Shionogi & Company, Limited
    Inventor: Kentaro Hirai
  • Patent number: 4412856
    Abstract: The novel compounds of the formula I are useful selective herbicides for postemergence application in crops of cereals, maize and rice.In formula I, ##STR1## A is an unsubstituted or substituted amino group, Q is a C.sub.2 -C.sub.6 alkylene bridge, Y is an oxygen or sulfur atom or an unsubstituted or substituted nitrogen atom, and Z is an unsubstituted or substituted phenyl, naphthyl or heterocyclic radical, which phenyl radical, containing the bridge member Y, can additionally carry one to four further substituents.
    Type: Grant
    Filed: May 22, 1981
    Date of Patent: November 1, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Georg Brunner, Rolf Schurter, Henry Szczepanski
  • 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: 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: 4377589
    Abstract: This disclosure describes substituted 2-alkylimino-3-alkyl-4-benzhydryl-4-thiazolidinols which are useful as diuretic agents.
    Type: Grant
    Filed: April 9, 1981
    Date of Patent: March 22, 1983
    Assignee: American Cyanamid Company
    Inventors: Andrew S. Tomcufcik, William B. Wright, Jr., Joseph W. Marsico, Jr.
  • 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: 4327110
    Abstract: Symmetrical N-substituted bis-carbamoyloximino disulfide compounds exhibit outstanding nematocidal, miticidal and insecticidal activity, coupled with substantially reduced mammalian toxicity and phytotoxicity as compared to known pesticidal compounds having a comparable spectrum of activity against insect, arachnid and nematode pests.
    Type: Grant
    Filed: March 28, 1977
    Date of Patent: April 27, 1982
    Assignee: Union Carbide Corporation
    Inventor: Themistocles D. J. D'Silva