The Five-membered Hetero Ring Consists Of Chalcogen, Plural Nitrogens, And Carbon Patents (Class 548/125)
  • Patent number: 5006540
    Abstract: Substituted 3-aminosydnonimines of the formula I ##STR1## and their pharmacologically acceptable acid addition salts, wherein R.sup.1 denotes, for example, alkyl having 1 to 8 C atoms, R.sup.2 denotes hydrogen or the radical --COR.sup.3 and R.sup.3 denotes, for example, an aliphatic radical having 1 to 4 C atoms, are prepared, for example, by cyclization of a compound of the formula II ##STR2## and if appropriate subsequent acylation and have useful pharmacological properties.
    Type: Grant
    Filed: October 17, 1989
    Date of Patent: April 9, 1991
    Assignee: Cassella Aktiengesellschaft
    Inventors: Karl Schonafinger, Rudi Beyerle, Melitta Just, Helmut Bohn, Jorg Ostrowski
  • Patent number: 5001138
    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: May 4, 1989
    Date of Patent: March 19, 1991
    Assignee: Nihon Tokushu Noyaku Seizo, K.K.
    Inventors: Kozo Shiokawa, Shinichi Tsuboi, Shinzo Kagabu, Koichi Moriya
  • Patent number: 4996316
    Abstract: A process for the preparation of tertiary N,N-dimethylamines by the reaction of primary amines, formaldehyde, and hydrogen under pressure and at elevated temperature in the presence of a nickel-containing hydrogenation catalyst in the liquid phase. The hydrogenation catalyst is suspended in a solvent, the nickel concentration is 0.1 to 10% by weight, based on the primary amine. The starting materials are separate from each other, brought to 80.degree. to 150.degree. C. and 1 to 15 MPa and fed into the catalyst suspension simultaneously with stirring and reacted in one step to form the tertiary N,N-dimethylamines.
    Type: Grant
    Filed: December 24, 1988
    Date of Patent: February 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
  • Patent number: 4952707
    Abstract: Chemiluminescent 1,2-dioxetane compounds are disclosed in which the molecule is stabilized at the 3-position on the dioxetane ring against decomposition prior to the molecule's coming in contact with a labile group-removing substance (e.g., an enzyme that will cleave the labile group to cause the molecule to decompose to form at least one light-emitting fluorophore) and substituted at the 4-position on the dioxetane ring with a fused polycyclic ring-containing fluorophore moiety bearing a labile ring substituent whose point of attachment to the fused polycyclic ring, in relation to this ring's point(s) of attachment to the dioxetane ring, is such that the total number of ring atoms separating these points of attachment, including the ring atoms at the points of attachment, is an odd whole number. These odd pattern substituted compounds decompose to emit light of greater intensity and of a different wavelength than that emitted by the corresponding even pattern substituted isomers.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: August 28, 1990
  • Patent number: 4937244
    Abstract: Substituted 3-aminosydnonimines of the formula I ##STR1## and their pharmacologically acceptable acid addition salts wherein A denotes, for example, --CH.sub.2 --,R.sup.1 denotes hydrogen or the radical --COR.sup.7,R.sup.2, R.sup.3, R.sup.4 and R.sup.5 denote alkyl with 1 to 4 C atoms andR.sup.7 denotes, for example, an aliphatic radical and 1 to 4 C atoms, are prepared by cyclization of a compound of the formula II ##STR2## and if appropriate subsequent acylation and have useful pharmacological properties. The invention includes pharmaceutical preparations containing the present compounds, and the use thereof for treating patients having cardiovascular ailments.
    Type: Grant
    Filed: August 3, 1988
    Date of Patent: June 26, 1990
    Assignee: Cassella Aktiengesellschaft
    Inventors: Karl Schonafinger, Rudi Beyerle
  • Patent number: 4902335
    Abstract: Herbicidal benzo-fused cyclic compounds of the formula ##STR1## wherein Q is ##STR2## Y is O or S, W is ##STR3## T is O, S, --NH-- or ##STR4## and R.sup.4 may represent, together with T, chlorine,Z is O or S,X is hydrogen or halogen,n is 0 or 1 andR is C.sub.3-6 cycloalkyl, an optionally substituted 5-membered heterocyclic group or an optionally substituted 6-membered heteroaromatic group which contains one to three nitrogen atoms,and salts thereof.
    Type: Grant
    Filed: June 17, 1988
    Date of Patent: February 20, 1990
    Assignee: Nihon Tokushu Noyaku Seizo K.K.
    Inventors: Toyohiko Kume, Toshio Goto, Atsumi Kamochi, Akihiko Yanagi, Shigeki Yagi, Hiroshi Miyauchi, Katsuhiko Shibuya
  • Patent number: 4888333
    Abstract: Substituted allylmercaptoacetylsydnonimines of the general formula I ##STR1## and their pharmacologically acceptable acid addition salts, in which R.sub.1 represents a secondary amino group of the formula ##STR2## and X denotes ##STR3## R.sub.2 denotes one of the radicals R.sub.3 OOC--, R.sub.4 SO.sub.2 -- or alkyl having1-4 C atoms,n denotes one of the values 1, 1 or 2,and R.sub.3 denotes alkyl having 1-4 C atoms,and R.sub.4 represents R.sub.3 or (R.sub.3).sub.2 N--, have valuable pharmacological properties.
    Type: Grant
    Filed: August 10, 1988
    Date of Patent: December 19, 1989
    Assignee: Cassella Aktiengessellschaft
    Inventors: Helmut Bohn, Melitta Just, Rolf-Eberhard Nitz
  • Patent number: 4886823
    Abstract: Acaricidal 1-arylfurazanyl-3-(2-alkyl-4-halogenoalkoxyphenyl)-(thio)ureas of the formula ##STR1## in which Q stands for oxygen or sulphur,R.sup.1 stands for hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio or halogenoalkylthio, andR.sup.2 stands for hydrogen, halogen, alkyl or alkoxy, orR.sup.1 and R.sup.2 together stand for alkylenedioxy which is optionally substituted by halogen,R.sup.3 stands for alkyl andR.sup.4 stands for alkyl which is substituted by fluorine and optionally in addition by chlorine and/or bromine.The corresponding isocyanates of the formula ##STR2## are also new.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: December 12, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Albrecht Marhold, Ulrike Wachendorff-Neumann
  • Patent number: 4853397
    Abstract: Insecticidal and acaricidal novel substituted furazans of the formula ##STR1## n which R.sup.1 and R.sup.2 are identical or different and represent hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or optionally substituted aryloxy, orR.sup.1 and R.sup.2 together represent an optionally substituted alkylene radical which is interrupted by 1 or 2 oxygen atoms or is bonded to the phenyl radical via 1 or 2 oxygen atoms,R.sup.3 and R.sup.4 are identical or different and represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl or halogenoalkoxy,R.sup.5 represents optionally substituted cycloalkyl, andX represents oxygen or sulphur.Intermediates of the formula ##STR2## in which B is --NH.sub.2, --NO.sub.2 or --NCX,R.sup.3 and R.sup.4 are identical or different and represent hydrogen, halogen, alkyl, alkoxy, halogenoalkyl or halogenoalkoxy,R.sup.
    Type: Grant
    Filed: June 25, 1987
    Date of Patent: August 1, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Albrecht Marhold, Robert Steffens
  • Patent number: 4851406
    Abstract: The present invention provides indole derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or an alkyl, alkenyl, cycloalkyl, cycloalkenyl, carboxyl, cyano, alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl or aryl radical, R.sub.2 is a hydrogen atom or an alkyl, trihalogenomethyl, hydroxyl, cycloalkyl, cyano, carboxyl, alkoxycarbonyl, alkylcarbonyl, aminocarbonyl, alkylaminocarbonyl or dialkylaminocarbonyl radical; R.sub.2 is a heterocyclic five-membered ring containing 1 to 4 heteroatoms or a heterocyclic six-membered ring containing 1 to 5 heteroatoms, the heteroatoms of the five- and six-membered rings being the same or different and being nitrogen, oxygen or sulphur and one or more of the nitrogen atoms optionally carrying an oxygen atom, the said five- and six-membered rings optionally being substituted by one or more alkyl, alkoxy, alkylthio, oxo, hydroxyl, nitro, amino, halogen or cyano groups; or R.sub.
    Type: Grant
    Filed: September 4, 1986
    Date of Patent: July 25, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Wolfgang von der Saal, Walter-Gunar Friebe, Bernd Muller-Beckmann, Gisbert Sponer
  • Patent number: 4845091
    Abstract: Optically active substituted 3-aminosydnonimines of the general formula I ##STR1## and their pharmacologically acceptable acid addition salts, wherein R.sup.1 denotes, for example, the radical R.sup.3 (R.sup.4)N-,R.sup.2 denotes the radical 1-methoxyethyl (--CH(CH.sub.3)OCH.sub.3), acetoxy-phenyl-methyl (--CH(C.sub.6 H.sub.5)O--COCH.sub.3), 1-(ethoxycarbonyl)-ethoxy (--O--CH.sub.3)CO.sub.2 C.sub.2 H.sub.5),R.sup.3 denotes alkyl(C.sub.1 -C.sub.4) andR.sup.4 denotes for example alkyl(C.sub.1 -C.sub.4),possess valuable pharmaceutical properties.
    Type: Grant
    Filed: July 14, 1986
    Date of Patent: July 4, 1989
    Assignee: Cassella Aktiengesellschaft
    Inventors: Karl Schonafinger, Rudi Beyerle, Helmut Bohn, Melitta Just, Piero Martorana, Rolf-Eberhard Nitz
  • Patent number: 4835280
    Abstract: The present invention provides Indolines of the formula: ##STR1## ps useful to provide pharmaceutically active pyrrolobenzimidazoles or tautomers thereof, of the formula: These compounds are useful for treating heart or circulatory diseases, especially those which respond to a change of blood pressure, an increase in cardiac output and/or a change in micro-circulation.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: May 30, 1989
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Martens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckman, Klaus Strein, Egon Roesch
  • Patent number: 4832732
    Abstract: Novel herbicidal 1-methyl-1H-imidazole -5-carboxylic acid derivatives, compositions containing these compounds as active ingredients, and a method for controlling weeds, preferably selectively in crops of useful plants. Further the invention also relates to a process for making these novel compounds.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: May 23, 1989
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: William R. Lutz, Guy R. E. Van Lommen, Victor Sipido, Wim G. Verschueren
  • Patent number: 4833252
    Abstract: Substituted N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'-triazinylureas of the general formula ##STR1## and the salts thereof with amines, alkali metal bases or alkaline earth metal bases, or with quaternary ammonium bases, have good pre- and postemergence selective herbicidal and growth regulating properties.In the above formula the symbols have the following meanings:R.sup.1 is hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 alkylsulfinyl, --CO--R.sup.8, --NR.sup.9 R.sup.10, --CO--NR.sup.11 R.sup.12 or --SO.sub.2 --NR.sup.13 R.sup.14,R.sup.2 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or cyano,R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sup.5 is hydrogen, C.sub.
    Type: Grant
    Filed: September 28, 1988
    Date of Patent: May 23, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Werner Topfl, Georg Pissiotas
  • Patent number: 4826988
    Abstract: Substituted furazans of the formula ##STR1## in which R and R.sup.1 are identical or different and represent optionally substituted aromatic or heteroaromatic radicals,R.sup.2 represents hydrogen, an OH or COOH grouping or an optionally substituted radical from the series comprising alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl, alkylsulphonyl, arylsulphonyl and aralkyl,Y represents oxygen or an S(O).sub.m, --CR.sup.3 R.sup.4, CO or NR.sup.5 grouping,in whichm represents the number 0, 1 or 2 andR.sup.3, R.sup.4 and R.sup.5 are identical or different andrepresent hydrogen or alkyl,n represents the number 0 or 1 andx represents oxygen or sulphur,and wherein, ifR represents phenyl,R.sup.1 represents phenyl,R.sup.2 represents hydrogen andx represents oxygen or sulphur,thenn represents the number 1,or ifn represents the number 0,R represents 4-bromophenyl,R.sup.1 represents 4-chlorophenyl andR.sup.2 represents hydrogen,thenX represents sulphur, which possess pesticidal activity.
    Type: Grant
    Filed: April 28, 1987
    Date of Patent: May 2, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Gerhard Zoebelein, Benedikt Becker, Wilhelm Stendel
  • Patent number: 4826992
    Abstract: 2,3-(Dihydro) bicyclic pyrazolidinones are intermediates for bicyclic pyrazolidinone antimicrobials.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: May 2, 1989
    Assignee: Eli Lilly and Company
    Inventors: Louis N. Jungheim, Sandra K. Sigmund
  • Patent number: 4801718
    Abstract: N-Aryl benzamides wherein the aryl group is a nitrogen containing heterocycle are useful as selective herbicidal agents. Compositions containing the novel benzamides and a herbicidal method of selective weed control are disclosed.
    Type: Grant
    Filed: December 5, 1985
    Date of Patent: January 31, 1989
    Assignee: Eli Lilly and Company
    Inventor: Kenneth W. Burow, Jr.
  • Patent number: 4775406
    Abstract: The salts of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring, of the general formula (I) ##STR1## exhibit a good plant growth-regulating activity. In the general formula the symbols have the following meaning:Y is an ammonium ion substituted up to fourfold by (substituted) alkyl, (substituted) alkenyl, alkynyl, (substituted) cycloalkyl, cycloalkenyl, and (substituted) phenyl, wherein the charged N may be part of a heterocyclic radial (NH.sub.4.sup.+ is excepted); phosphonium ion substituted fourfold by alkyl, (substituted) phenyl or (substituted) benzyl; sulfonium- or sulfoxonium ion substituted threefold by alkyl, (substituted) phenyl or (substituted) benzyl; the guanidinium ion or an O-alkylisourea cation;R.sup.1, R.sup.2 independently of each other are alkyl;R.sup.3 is alkyl, alkoxy or halogen; andn is 0, 1, 2 or 3.
    Type: Grant
    Filed: November 21, 1985
    Date of Patent: October 4, 1988
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Roland Schmierer, Ernst-Friedrich Schulze, Helmut Bustell, Erwin Hacker
  • Patent number: 4772309
    Abstract: A 5-Acylamino-pyrazole derivatives of the formula ##STR1## in which R.sup.1 represents hydrogen, halogen or nitro,R.sup.2 represents hydrogen, alkyl, alkenyl, alkinyl or optionally substituted cycloalkyl,R.sup.3 represents hydrogen or alkyl,R.sup.4 represents hydrogen or alkyl,X represents oxygen or sulphur,n represents the integer 0, 1 or 2,Ar represents in each case optionally substituted phenyl or pyridyl andHet represents an optionally substituted 5- or 6- membered heterocyclic radical linked via a carbon atom,which exhibit herbicidal and plant growth regulating activity.
    Type: Grant
    Filed: March 19, 1987
    Date of Patent: September 20, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Reinhold Gehring, Otto Schallner, Hans-Joachim Santel, Robert R. Schmidt, Klaus Lurssen
  • Patent number: 4772719
    Abstract: A novel process for the preparation of 3-bromo- and 3-chloro-5-substituted isoxazoles is provided. Dibromo- or dichloro-formaldoxime is reacted with an excess of an 1-alkyne derivative of the formulaR--C.tbd.CHwhere R is hydrogen, phenyl or 1-6 C alkyl optionally substituted by halogen, OH, OR', CHO, COR', COOR', CONH.sub.2, CONR'R" or NHCOR' where, in turn, R' and R", which may be the same or different, are a 1-6 C alkyl or haloalkyl, in the presence of (i) at least an equimolecular amount, with respect to the dibromo- or dichloro-formaldoxime, of an alkaline base selected from the class consisting of sodium and potassium carbonate and bicarbonate and (ii) an inert solvent in which the 1-alkyne is soluble at room temperature.
    Type: Grant
    Filed: July 24, 1986
    Date of Patent: September 20, 1988
    Assignee: Zambon S.p.A.
    Inventors: Dario Chiarino, Alberto Sala, Mauro Napoletano
  • Patent number: 4764524
    Abstract: Insecticidally and acaricidally active novel substituted furazanes of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio or optionally substituted aryloxy, orR.sup.1 and R.sup.2 together are an optionally substituted alkylene radical which is interrupted by 1 or 2 oxygen atoms,R.sup.3 and R.sup.4 each independently is hydrogen, alkyl, alkoxy, halogenoalkyl or halogenoalkoxy, andX is oxygen or sulphur.
    Type: Grant
    Filed: January 8, 1986
    Date of Patent: August 16, 1988
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Rudolph Braden, Heinz Ziemann, Gerhard Zoebelein, Wolfgang Pfluger
  • 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: 4714707
    Abstract: Aryl substituted diazaheterocyclic amines and their use in the treatment of gastrointestinal motility dysfunctions.
    Type: Grant
    Filed: January 13, 1984
    Date of Patent: December 22, 1987
    Assignee: Rorer Pharmaceutical Corporation
    Inventors: Donald E. Kuhla, William L. Studt, Henry F. Campbell, John Yelnosky
  • Patent number: 4713393
    Abstract: Phenylalkyl-2,3-dihydrobenzofurans and analogs were prepared by (1) nucleophilic substitution involving an appropriately substituted 2,3-dihydrobenzofuranol (or 2,3-dihydrobenzopyranol) and a cinnamylhalide followed by reduction; or (2) by Wittig reaction involving a halomethyl derivative of 2,3-dihydrobenzofuran (or 2,3-dihydrobenzopyran and an aryl or a heteroaryl aldehyde followed by reduction. These compounds were found to be potent anti-inflammatory agents.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: December 15, 1987
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Kathryn L. Thompson, David A. Boulton
  • Patent number: 4703125
    Abstract: A carbonyl compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, aryl, substituted aryl or a straight-chain or cyclic, saturated or unsaturated aliphatic hydrocarbon radical, which is optionally interrupted by O, S, N, N-alkyl, N-aryl or N-aralkyl, and which is optionally substituted by hydroxyl, alkoxy, alkyl, trifluoromethyl, halogen, phenyl, alkoxycarbonyl or dialkylamino, the two alkyl radicals together with the nitrogen atom optionally forming a 5 to 7-membered ring, which optionally contains a heteroatom from the group comprising O, S, NH or N-alkyl and these aforementioned alkyl and phenyl radicals in turn optionally being substituted by halogen, trifluoromethyl, alkyl, aryl, aralkyl, alkoxy, alkylmercapto or SO.sub.2 -alkyl,R.sup.2 represents the radical CXR.sup.8, R.sup.8 having the meaning indicated for R.sup.1 and being identical to or different from R.sup.1, and X representing oxygen, sulphur or the radical NR.sup.9 R.sup.10, R.sup.9 and R.sup.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: October 27, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Ingendoh, Horst Meyer, Bernward Garthoff
  • Patent number: 4699916
    Abstract: Substituted furazans of the formula ##STR1## in which R and R.sup.1 are identical or different and represent optionally substituted aromatic or heteroaromatic radicals,R.sup.2 represents hydrogen, an OH or COOH grouping or an optionally substituted radical from the series comprising alkyl, alkoxy, cycloalkyl, cycloalkenyl, alkoxycarbonyl, alkoxythiocarbonyl, alkylsulphonyl, arylsulphonyl and aralkyl,Y represents oxygen or an S(O).sub.m, --CR.sup.3 R.sup.4, CO or NR.sup.5 grouping,in whichm represents the number 0, 1 or 2 andR.sup.3, R.sup.4 and R.sup.5 are identical or different and represent hydrogen or alkyl,n represents the number 0 or 1 andX represents oxygen or sulphur,and wherein, ifR represents phenyl,R.sup.1 represents phenyl,R.sup.2 represents hydrogen andX represents oxygen or sulphur,thenn represents the number 1,or ifn represents the number 0,R represents 4-bromophenyl,R.sup.1 represents 4-chlorophenyl andR.sup.2 represents hydrogen,thenX represents sulphur,which possess pesticidal activity.
    Type: Grant
    Filed: January 21, 1986
    Date of Patent: October 13, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wilhelm Sirrenberg, Erich Klauke, Gerhard Zoebelein, Benedikt Becker, Wilhelm Stendel
  • Patent number: 4695567
    Abstract: The present invention provided pyrrolobenzimidazoles or tautomer thereof, of the general formula: ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.3 -C.sub.7 cycloalkyl;R.sub.2 is hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, or a carbonyl group substituted by hydroxyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyoxy, amino, C.sub.1 -C.sub.6 alkylamino, C.sub.2 -C.sub.12 dialkylamino or hydrazino, orR.sub.2 and R.sub.1 together with the carbon to which they are attached form a C.sub.3 -C.sub.8 spirocycloalkyl ring, or R.sub.1 and R.sub.2 together form C.sub.3 -C.sub.7 alkylidene or C.sub.3 -C.sub.7 cycloalkylkidene,X is a valency bond, C.sub.1 -C.sub.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: September 22, 1987
    Assignee: Boehringer Mannheim GmbH
    Inventors: Alfred Mertens, Jens-Peter Holck, Herbert Berger, Bernd Muller-Beckmann, Klaus Strein, Egon Roesch
  • Patent number: 4692513
    Abstract: Alpha-L-Aspartyl-D-heteroaromatic-substituted glycine esters and amides are disclosed to be useful as high intensity sweeteners. These compounds can be used to sweeten a variety of foods, beverages and other oral products.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: September 8, 1987
    Assignee: The Procter & Gamble Company
    Inventors: Robert B. Blum, John M. Gardlik, John M. Janusz, George P. Rizzi
  • Patent number: 4666502
    Abstract: The invention provides 5-membered heteroaromatic compounds of formula IArN(Y)COCH.sub.2 Cl Iwherein Ar is a 5-membered heteroaromatic group comprising 1 or 2 heteroatoms selected from O, S and N and linked by a ring C-atom to the N-atom of the N(Y)COCH.sub.2 Cl group to which it is bound, whereby where Ar is pyrazolyl, said N(Y)COCH.sub.2 Cl group is in the 4-position,and Y is as specified in the description,the use of these compounds as herbicides, compositions for facilitating such use and the preparation of the chloroacetamides.
    Type: Grant
    Filed: February 3, 1983
    Date of Patent: May 19, 1987
    Assignee: Sandoz Ltd.
    Inventors: Karl Seckinger, Fred Kuhnen, Karlheinz Milzner
  • Patent number: 4654431
    Abstract: A novel photocurable monomer having the formula: ##STR1## wherein: Ar is arylene;R.sup.1 is H, alkyl, alkoxy, amino, halogen, sulfide, sulfoxide, sulfonate, aryl or heterocyclic;R.sup.2 is H, alkyl, aryl or aralkyl; andR.sup.3 is H or methyl,is useful in preparing a polymer having a high refractive index. The polymer is useful in optical components, such as lenses.
    Type: Grant
    Filed: September 10, 1982
    Date of Patent: March 31, 1987
    Assignee: Eastman Kodak Company
    Inventor: Charles D. DeBoer
  • Patent number: 4636505
    Abstract: Acylanilides of the formula ##STR1## wherein R.sup.1 and R.sup.2, the same or different, each is cyano, carbamoyl, nitro, halogeno, perfluoroalkyl or other defined substituents;R.sup.3 is hydrogen or halogen;R.sup.4 is hydrogen or alkyl, or is joined to R.sup.5 ;R.sup.5 is hydrogen, hydroxy, alkoxy or acyloxy or is joined to R.sup.4 ;R.sup.6 is alkyl or halogenoalkyl, or has the formula --A.sup.3 --R.sup.8 or --A.sup.4 --X.sup.2 --A.sup.5 --R.sup.9 ;A.sup.1 and A.sup.4, the same or different, each is alkylene;A.sup.2, A.sup.3 and A.sup.5, the same or different, each is a direct link or alkylene;X.sup.1 and X.sup.2, the same or different, each is oxygen, sulphur, sulphinyl, sulphonyl, imino or alkylimino;R.sup.7 and R.sup.9, the same or different, each is alkyl, alkenyl, hydroxyalkyl, cycloalkyl, phenyl optionally substituted, naphthyl or heterocyclic optionally substituted;and R.sup.8 is phenyl, naphthyl or heterocyclic as defined above for R.sup.7 or R.sup.
    Type: Grant
    Filed: July 15, 1983
    Date of Patent: January 13, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventor: Howard Tucker
  • Patent number: 4629495
    Abstract: Herbicidal compounds of the formula: ##STR1## wherein A represents R.sup.1 R.sup.2 N-- (wherein R.sup.1 represents C.sub.1-8 alkyl or C.sub.2-8 alkenyl or alkynyl unsubstituted or substituted by CN, OH, C.sub.1-6 alkoxy, carboxy, C.sub.2-9 alkoxycarbonyl, aminocarbonyl optionally substituted by C.sub.1-8 alkyl or C.sub.2-8 alkenyl, C.sub.1-8 alkoxyaminocarbonyl, C.sub.1-8 alkanesulphonamidocarbonyl, --C(.dbd.O)Het, where Het represents a nitrogen-containing heterocyclic group, or one or more halogen atoms or R.sup.1 represents C.sub.3-6 cycloalkyl optionally substituted by C.sub.1-4 alkyl and R.sup.2 represents H or R.sup.1, or R.sup.1 represents C.sub.1-4 alkylthio and R.sup.2 represents H, or A represents R.sup.p (R.sup.q)--C.dbd.N-- (wherein R.sup.p represents C.sub.1-4 alkoxy or amino substituted by one or two C.sub.1-4 alkyl groups and R.sup.q represents H or C.sub.1-4 alkyl) or A represents 2-oxo-azetidin-1-yl, 2-oxo-pyrrolidin-1-yl or 2-oxo-piperidin-1-yl optionally substituted by C.sub.
    Type: Grant
    Filed: July 13, 1983
    Date of Patent: December 16, 1986
    Assignee: May & Baker Limited
    Inventors: Leslie R. Hatton, Edgar W. Parnell, David A. Roberts
  • Patent number: 4614534
    Abstract: 5-Amino-4-heterocyclyl-1-phenylpyrazoles of the formula ##STR1## in which R.sup.1 represents hydrogen or alkyl,R.sup.2 represents hydrogen or a radical ##STR2## R.sup.3 represents hydrogen, ##STR3## alkyl, alkenyl or alkinyl, R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 independently of one another represent hydrogen, cyano, nitro, halogen, alkyl, alkoxy, alkoxycarbonyl, halogenoalkyl, halogenoalkoxy or a radical --S(O).sub.n --R.sup.10,R.sup.9 represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, alkoxyalkyl, alkylthioalkyl, optionally substituted cycloalkyl, optionally substituted aryl, alkoxy, alkylthio, optionally substituted aryloxy or aryloxyalkyl, optionally substituted arylthio, alkylamino, dialkylamino or optionally substituted arylamino,R.sup.
    Type: Grant
    Filed: June 4, 1985
    Date of Patent: September 30, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jorg Stetter, Reinhold Gehring, Markus Lindig, Otto Schallner, Ludwig Eue, Robert R. Schmidt, Hans-Joachim Santel, Klaus Lurssen
  • Patent number: 4604132
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: A, B and D are selected from CH and N;E is selected from oxygen and sulfur;X are selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, alkanoyloxy, benzyloxy, substituted benzyloxy, phenyl, substituted phenyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;R.sup.1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation;R.sup.2 is selected from alkyl substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl;R.sup.
    Type: Grant
    Filed: April 27, 1984
    Date of Patent: August 5, 1986
    Assignee: ICI Australia Limited
    Inventors: Richard J. Conway, Keith G. Watson, Graeme J. Farquharson
  • Patent number: 4588817
    Abstract: Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.
    Type: Grant
    Filed: June 4, 1984
    Date of Patent: May 13, 1986
    Assignee: The Upjohn Company
    Inventors: Barney J. Magerlein, Howard A. Whaley
  • Patent number: 4556649
    Abstract: Insecticidally active novel substituted malonic acid diamide insecticides of the formula ##STR1## wherein R.sup.1 represents aryl or heteroaryl, each of which can optionally be substituted,R.sup.2 represents hydrogen or trialkylsilyl, and represents alkyl, cycloalkyl, alkenyl, alkinyl, aralkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphenyl, arylsulphenyl, alkylsulphonyl, arylsulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, arylaminosulphonyl or arylalkylaminosulphonyl, each of which can optionally be substituted, and represents radicals of the formula--CO--NR.sup.5 R.sup.6whereinR.sup.5 and R.sup.6 independently of one another represent hydrogen, alkyl, cycloalkyl, aryl, alkylaminocarbonyl, arylaminocarbonyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylsulphonyl or arylsulphonyl, it being possible for these radicals to be optionally substituted,R.sup.3 represents hydrogen or the radical R.sup.4,R.sup.7 and R.sup.
    Type: Grant
    Filed: December 21, 1984
    Date of Patent: December 3, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Salzburg, Rudolf Fauss, Kurt Findeisen, Bernhard Homeyer
  • Patent number: 4529721
    Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: July 16, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
  • Patent number: 4507485
    Abstract: Histamine H.sub.2 -antagonists of the formula: ##STR1## wherein m is an integer of from 0 to 2 inclusive;n is an integer of from 2 to 5 inclusive;Z is oxygen, sulfur or methylene; andA is ##STR2## in which R.sup.1 is hydrogen, (lower)alkyl, or (lower)alkoxy, and R.sup.2 is ##STR3## in which q is an integer of from 1 to 4 inclusive, and R.sup.3 and R.sup.4 each are independently, (lower)alkyl, (lower)-alkoxy(lower)alkyl in which the (lower)alkoxy moiety is at least two carbon atoms removed from the nitrogen atom, cyclo(lower)alkyl, or phenyl(lower)alkyl; provided that R.sup.3 and R.sup.4 may not both be cyclo(lower)alkyl; or R.sup.3 and R.sup.4, taken together with the nitrogen atom to which they are attached, may be pyrrolidino, methylpyrrolidino, dimethylpyrrolidino, morpholino, thiomorpholino, piperidino, methylpiperidino, dimethylpiperidino, N-methylpiperazino, 1,2,3,6-tetrahydropyridyl, homopiperidino, heptamethyleneimino, octamethyleneimino, or 3-azabicyclo[3.2.
    Type: Grant
    Filed: January 23, 1984
    Date of Patent: March 26, 1985
    Assignee: Bristol-Myers Company
    Inventors: Ivo Monkovic, Ronnie R. Crenshaw
  • Patent number: 4501894
    Abstract: Novel heterocyclic compounds of the formula ##STR1## wherein X is selected from the group consisting of chlorine, bromine, iodine and --OH, W is selected from the group consisting of hydrogen and --CN, Z is selected from the group consisting of --CH.sub.2 -- and --O-- attached to the carbon atom included between a nitrogen and the sulfur atom of Y and Y is selected from the group consisting of thiazolyl or thiadiazolyl connected to ##STR2## at one of its available positions except for (2-benzyl-4 and 5-thiazolyl) methanol and .alpha.-cyano-(2-benzyl-5-thiazolyl)-methanol and the compounds wherein X is halogen when W is --CN whose esters have insecticidal activity.
    Type: Grant
    Filed: February 25, 1982
    Date of Patent: February 26, 1985
    Assignee: Roussel Uclaf
    Inventors: Francois Nezot, Pierre Girault, Jean Tessier, Jacques Martel
  • Patent number: 4496737
    Abstract: A process is disclosed for preparing intermediates which are useful for obtaining sulfamylamidine antisecretory agents.
    Type: Grant
    Filed: September 27, 1982
    Date of Patent: January 29, 1985
    Assignee: Merck & Co., Inc.
    Inventor: Jacob M. Hoffman, Jr.
  • Patent number: 4489093
    Abstract: Novel esters in all possible isomeric forms of the formula ##STR1## wherein R is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkyl-alkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, ##STR2## aryl optionally substituted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, ##STR3## R' is alkyl of 1 to 8 carbon atoms, R" and R"' are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.sub.3 are individually alkyl of 1 to 18 carbon atoms (b) aryl of 6 to 14 carbon atoms optionally substituted with at least one substituent selected from the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --OCF.sub.3, --CF.sub.3 and --SCF.sub.
    Type: Grant
    Filed: May 17, 1983
    Date of Patent: December 18, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4450217
    Abstract: Novel chalcogenopentalene compounds having a tellurium atom in the 6a position, and methods of making chalcogenopentalenes having a tellurium or a selenium atom in the 6a position are disclosed. The chalcogenopentalene compounds are useful as sensitizers in electrophotographic compositions and elements containing an electron donor and as charge emitters in multilayer photoconductive elements.
    Type: Grant
    Filed: March 15, 1983
    Date of Patent: May 22, 1984
    Assignee: Eastman Kodak Company
    Inventors: Michael R. Detty, Jerome H. Perlstein
  • Patent number: 4448970
    Abstract: Novel antibacterially-active analogs of the antibiotics nodusmicin and nargenicin A.sub.1. These compounds are prepared by selectively blocking active hydroxyl groups at the 9, 11 and 18 positions of nodusmicin, and the 11 and 18 positions of nargenicin A.sub.1. Antibacterially-active compounds can be used in various environments to control or eradicate susceptible bacteria. The techniques for such use are well known in the art.
    Type: Grant
    Filed: May 4, 1981
    Date of Patent: May 15, 1984
    Assignee: The Upjohn Company
    Inventor: Barney J. Magerlein
  • Patent number: 4446322
    Abstract: This application provides a novel process for the synthesis of 3-(2-hydroxy-2-phenylethyl)-N-[(phenylamino)carbonyl]sydnonimine derivatives and novel hydrophobic and hydrophilic acyl derivatives thereof as pro-drug central nervous system stimulants.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: May 1, 1984
    Assignee: American Home Products Corporation
    Inventor: Reinhardt P. Stein
  • Patent number: 4436743
    Abstract: Pharmacologically-active 3-aminosydnonimines (which are optionally substituted in the N.sup.6 -position) and their physiologically-acceptable acid-addition salts are compounded into standard dosage-form medicament compositions and are useful for prophylaxis for and treatment of cardiovascular-system disorders, such as high blood pressure and angina pectoris. The 3-aminosydnonimines are 3-[4-(lower alkoxy)carbonylpiperazin-1-yl]sydnonimines and 3-[N-(lower alkyl)-N-(tetrahydro-3-thienyl S,S-dioxide)]-sydnonimines.
    Type: Grant
    Filed: February 19, 1982
    Date of Patent: March 13, 1984
    Assignee: Cassella Aktiengesellschaft
    Inventors: Karl Schonafinger, Rudi Beyerle, Helmut Bohn, Melitta Just, Piero A. Martorana, Rolf-Eberhard Nitz
  • Patent number: 4430342
    Abstract: An N-acyl-3-[4-(benzoylalkyl)piperazin-1-yl]-sydnonimine compound represented by the following formula ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,R.sup.2 represents a lower alkyl group,a lower alkoxy group or a phenyl group, andn represents zero or an integer of 1 to 10,and its acid addition salt. The above sydnonimine compounds are useful for the treatment of troubles of the circulatory system and can be produced by contacting a 3-[4-(benzoylalkyl)-piperazin-1-yl]sydnonimine compound represented by the following formula ##STR2## wherein R.sup.1 and n are as defined, with a carboxylic acid represented by the following formulaR.sup.2 COOHwherein R.sup.2 is as defined.
    Type: Grant
    Filed: September 21, 1982
    Date of Patent: February 7, 1984
    Assignee: Hiroyoshi Hidaka
    Inventors: Hiroyoshi Hidaka, Ikuo Matsumoto, Junji Yoshizawa, Shigenori Kotani
  • Patent number: 4421754
    Abstract: A 3-[4-(benzoylalkyl)piperazin-1-yl]sydnonimine compound represented by the following formula ##STR1## wherein R represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and n represents zero or an integer of 1 to 10,and its acid addition salt. The above sydnonimine compounds are useful for the treatment of troubles of the circulatory system and can be produced by contacting a 4-(benzoylalkyl)-1-(N-nitrosocyanomethylamino)piperazine represented by the following formula ##STR2## wherein R and n are as defined, with an acid.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: December 20, 1983
    Assignee: Hiroyoshi Hidaka
    Inventors: Hiroyoshi Hidaka, Ikuo Matsumoto, Junji Yoshizawa, Shigenori Kotani
  • Patent number: 4416893
    Abstract: Pharmaceutical compositions comprising as pharmacologically active component a 1,2,5-oxadiazole-2-oxide of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 have the following meaning:______________________________________ R.sup.1 R.sup.2 ______________________________________ 1. CO--NH.sub.2 CH.sub.3 2. COOC.sub.2 H.sub.5 CH.sub.3 3. CO--NHNH.sub.2 CH.sub.3 4. COOH CH.sub.3 5. --NH--COOC.sub.2 H.sub.5 CH.sub.3 6. --NH--COOC.sub.3 H.sub.7 (n) CH.sub.3 7. --NH--COOC.sub.3 H.sub.7 (i) CH.sub.3 8. --NH--COOC.sub.4 H.sub.9 (n) CH.sub.3 9. --NH--COOCH.sub.2 --phenyl CH.sub.3 10. CO--NH.sub.2 CO--NH.sub.2 11. CN CN 12. COOH COOCH.sub.3 13. COOCH.sub.3 COOCH.sub.3 14. COOC.sub.2 H.sub.5 COOC.sub.2 H.sub.5 15. CH.sub.3 CO--NH.sub.2 16. CH.sub.3 COOC.sub.2 H.sub.5 17. CH.sub.3 CO--NHNH.sub.2 18. CH.sub.3 COOH 19. CN CO--NH.sub.2 20. CO--NH--phenyl CO--NH--phenyl 21. CH.sub.3 NH--COOC.sub.2 H.sub.5 22. CH.sub.3 NH--COOC.sub.3 H.sub.7 (n) 23. CH.sub.3 NH--COOC.sub.3 H.sub.7 (i) 24. CH.sub.3 NH--COOC.sub.4 H.
    Type: Grant
    Filed: March 24, 1981
    Date of Patent: November 22, 1983
    Assignee: Cassella Aktiengesellschaft
    Inventors: Karl Schonafinger, Rudi Beyerle, Anton Mogilev, Helmut Bohn, Piero Martorana, Rolf-Eberhard Nitz
  • Patent number: 4416683
    Abstract: N-Aryl benzamides wherein the aryl group is a nitrogen containing heterocycle are useful as selective herbicidal agents. Compositions containing the novel benzamides and a herbicidal method of selective weed control are disclosed.
    Type: Grant
    Filed: September 14, 1981
    Date of Patent: November 22, 1983
    Assignee: Eli Lilly and Company
    Inventor: Kenneth W. Burow, Jr.
  • Patent number: RE32154
    Abstract: Production of new 2-(o-alkylthiophenyl)-1,3-diazacycloalkene hydrohalides by reaction of a benzo-thietane-2-spiro-2'-(1',3'-diazacycloalkane) with an alkyl halide, and the new 2-(o-alkylthiophenyl)-1,3-diazacycloalkene hydrohalides which are pharmaceuticals, auxiliaries for the textile and rubber industries, plant protection agents and starting materials for the production of pharmaceuticals, plant protection agents and dyes.
    Type: Grant
    Filed: February 25, 1981
    Date of Patent: May 20, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Hagen, August Amann, Hubert Giertz