From A Ketene (hch=c=o, Wherein H May Be Substituted) Patents (Class 549/329)
  • Patent number: 9562027
    Abstract: Device and method for continuously preparing high-purity AKD without solvent includes a reactor making continuous mixing of raw materials. The process includes: the tertiary amine feeding into the reactor and the continuously feeding acyl chloride from three to ten line; under operating state, the motor rotates the internal cylinder in relation to external cylinder, forcing the fed materials to convey and stir in the conveying section of annular column passage, forcing the materials to shear and mix by movement of shearing and kneading blades. Arrangement of conveying and mixing sections along the axial direction of annular column passage, causes sufficient reaction of materials and controls the material temperature through internal and external heat exchange systems until the reaction products are discharged from outlet.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: February 7, 2017
    Assignee: SUZHOU TIANMA SPECIALTY CHEMICALS CO., LTD.
    Inventors: Baochi Sun, Anqi Tan
  • Patent number: 8871055
    Abstract: Disclosed is a sizing composition comprising a hydrophobic paper sizing agent and a hydrophobically modified poly(aminoamide). Also disclosed is a method of making the sizing composition and a method of using the sizing composition.
    Type: Grant
    Filed: March 30, 2012
    Date of Patent: October 28, 2014
    Assignee: Solenis Technologies, L.P.
    Inventor: Susan M. Ehrhardt
  • Patent number: 8563752
    Abstract: The invention relates to a method for the production of L-carnitine, wherein a chiral ?-lactone carnitine precursor is obtained by a [2+2] cycloaddition of ketene with an aldehyde X—CH2—CHO, wherein X is selected from Cl, Br, I and trimethylamine, in the presence of a chiral catalyst.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: October 22, 2013
    Assignee: Lonza Ltd.
    Inventors: Paul Hanselmann, Ellen Klegraf, Stephan Elzner, Wilhelm Quittmann, Daniel Friedrich Fischer
  • Patent number: 8512520
    Abstract: A paper size which comprises a stable aqueous dispersion of a reactive size, from 5 to 100% by weight, based on the reactive size, of a substantially linear nitrogen-comprising polymer having at least 3 mmol/g of basic nitrogen atoms, and from 1 to 50% by weight of cationic starch having a degree of substitution of at least 0.05 is described. The paper size has a good sizing effect and a stable viscosity.
    Type: Grant
    Filed: November 29, 2005
    Date of Patent: August 20, 2013
    Assignee: BASF Aktiengesellschaft
    Inventors: Markus Schmid, Roland Ettl, Klaus Lorenz, Rainer Dyllick-Brenzinger, Andreas Brockmeyer
  • Publication number: 20120196740
    Abstract: Bi-functional cobalt-containing catalysts useful for making stereo specific compounds and compositions, along with methods of making, and uses thereof in the syntheses of optically pure ?-lactones from aldehydes and ketene are described. Precursors, intermediates, compositions, and particular features of the use if the compositions, such as high enantiomeric selectivity, high yield and low mole percent of catalyst useful are provided.
    Type: Application
    Filed: June 7, 2010
    Publication date: August 2, 2012
    Applicant: UNIVERSITY OF TOLEDO
    Inventor: Yun-Ming Lin
  • Patent number: 8163133
    Abstract: The invention relates to an aqueous dispersion useful for internal sizing or surface sizing in the production of paper, comprising at least one cellulose reactive sizing agent selected from the group consisting of ketene dimers and multimers, at least one cellulose non-reactive sizing agent and at least one emulsifier selected from the group consisting of oxyalkylene phosphate and sulfate esters and salts thereof. The invention further concerns a process for its preparation, use thereof, and processes for the production of paper.
    Type: Grant
    Filed: March 26, 2004
    Date of Patent: April 24, 2012
    Assignee: Akzo Nobel N.V.
    Inventor: Ralf Krückel
  • Patent number: 8124794
    Abstract: The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.
    Type: Grant
    Filed: November 17, 2009
    Date of Patent: February 28, 2012
    Assignee: Sanford-Burnham Medical Research Institute
    Inventors: Jeffrey W. Smith, Fumiko Axelrod, Steven J. Kridel, Daniel Romo, Vikram Purohit, Gil Ma
  • Publication number: 20120022275
    Abstract: The invention relates to a method for the production of L-carnitine, wherein a chiral ?-lactone carnitine precursor is obtained by a [2+2] cycloaddition of ketene with an aldehyde X—CH2—CHO, wherein X is selected from Cl, Br, I and trimethylamine, in the presence of a chiral catalyst.
    Type: Application
    Filed: July 20, 2011
    Publication date: January 26, 2012
    Inventors: Paul Hanselmann, Ellen Klegraf, Stephan Elzner, Wilhelm Quittmann, Daniel Friedrich Fischer
  • Patent number: 7999123
    Abstract: An aldehyde derivative represented by the general formula (2) is reacted with ketene in the presence of a Lewis acid catalyst to produce a novel 2-oxetanone derivative (1), which is then purified to a 2-oxetanone derivative having a high trans-isomer purity, and then converted to a vinyl derivative (3) through decarboxylation reaction.
    Type: Grant
    Filed: May 17, 2007
    Date of Patent: August 16, 2011
    Assignees: JNC Corporation, Chisso Petrochemical Corporation
    Inventors: Yasuo Urata, Shunji Oshima, Ryousuke Nishibata, Keiichi Kodaki, Hiroyuki Takeuchi, Shuichi Matsui
  • Patent number: 7960497
    Abstract: The embodiments of the process of the present invention relate to the preparation of alkyl ketene dimers (AKD), where the process combines at least one polyamine with a fatty acid chloride in a molar ratio of less than one mole of polyamine to one mole of fatty acid chloride thereby forming an alkyl ketene dimer/amine salt that is subsequently separated into an organic dimer layer and an aqueous salt layer.
    Type: Grant
    Filed: January 3, 2007
    Date of Patent: June 14, 2011
    Assignee: Hercules Incorporated
    Inventor: David A. Gerstenhaber
  • Publication number: 20100173982
    Abstract: The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.
    Type: Application
    Filed: November 17, 2009
    Publication date: July 8, 2010
    Applicant: The Burnham Institute for Medical Research
    Inventors: Jeffrey W. Smith, Fumiko Axelrod, Steven J. Kridel, Daniel Romo, Vikram Purohit, Gil Ma
  • Patent number: 7728153
    Abstract: The present invention features methods of treating a cancer in a subject by administering an effective amount of a beta-lactone to the subject. The invention also features methods of inhibiting angiogenesis in a subject by administering an effective amount of an inhibitor of fatty acid synthase to the subject. These methods can be used to treat a variety of cancers and other diseases and conditions. The invention also features methods of identifying beta-lactones and other compounds that can be used in the methods of the invention for the treatment of tumors, inhibition of angiogenesis, and the treatment of diseases and conditions that involve pathological angiogenesis. The invention also features methods of synthesizing beta-lactones and features novel beta-lactone compounds.
    Type: Grant
    Filed: March 16, 2006
    Date of Patent: June 1, 2010
    Assignee: The Burnham Institute for Medical Research
    Inventors: Jeffrey W. Smith, Fumiko Axelrod, Steven J. Kridel, Daniel Romo, Vikram Purohit, Gil Ma
  • Publication number: 20090275756
    Abstract: An aldehyde derivative represented by the general formula (2) is reacted with ketene in the presence of a Lewis acid catalyst to produce a novel 2-oxetanone derivative (1), which is then purified to a 2-oxetanone derivative having a high trans-isomer purity, and then converted to a vinyl derivative (3) through decarboxylation reaction.
    Type: Application
    Filed: May 17, 2007
    Publication date: November 5, 2009
    Applicants: CHISSO CORPORATION, CHISSO PETROCHEMICAL CORPORATION
    Inventors: Yasuo Urata, Shunji Oshima, Ryousuke Nishibata, Keiichi Kodaki, Hiroyuki Takeuchi, Shuichi Matsui
  • Patent number: 6642394
    Abstract: (Meth)acrylic acid is reacted with a fatty acid anhydride and the resultant reaction mixture is neutralized and washed with an aqueous alkaline solution having a pH of 7.5 to 13.5. Thus, high-purity (meth)acrylic anhydride can be industrially advantageously produced while avoiding polymerization. This (meth)acrylic anhydride is reacted with a secondary or tertiary alcohol in the presence of a basic compound which in 25° C. water has an acidity (pKa) of 11 or lower. Thus, a high-purity (meth)acrylic ester can be produced in high yield.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: November 4, 2003
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventors: Naoshi Murata, Kimio Tamura, Yasukazu Yoshida, Motomu Ohkita
  • Patent number: 6316095
    Abstract: Fine paper that is sized with a 2-oxetanone alkaline sizing agent and that does not encounter machine feed problems in high speed converting or reprographic machines, including continuous forms bond paper and adding machine paper, processes for converting the paper into envelopes, continuous forms bond paper and adding machine paper, and paper products of the processes.
    Type: Grant
    Filed: October 18, 1999
    Date of Patent: November 13, 2001
    Assignee: Hercules Incorporated
    Inventors: Donald K. Black, Kyle J. Bottorff, Clement Linus Brungardt, David Howard Dumas, Susan Merrick Ehrhardt, John Charles Gast, Jian-Jian Zhang
  • Patent number: 6007906
    Abstract: Fine paper that is sized with a 2-oxetanone alkaline sizing agent and that does not encounter machine feed problems in high speed converting or reprographic machines, including continuous forms bond paper and adding machine paper, processes for converting the paper into envelopes, continuous forms bond paper and adding machine paper, and paper products of the processes.
    Type: Grant
    Filed: August 14, 1997
    Date of Patent: December 28, 1999
    Assignee: Hercules Incorporated
    Inventors: Kyle J. Bottorff, Clement Linus Brungardt, David Howard Dumas, Susan Merrick Ehrhardt, John Charles Gast, Jian-Jian Zhang
  • Patent number: 5998635
    Abstract: The present invention provides a process for producing a .beta.-lactone derivative by reacting an aldehyde represented by formula (1):RCHO (1)wherein R represents a C1-C15 alkyl group which may be substituted by an aryl group, a C2-C15 alkenyl group, a 5-7-membered alicyclic group, or a phenyl group which may be substituted by a C1-C4 alkyl group; and ketene in the presence of a transition metal-phosphine complex. An industrially valuable .beta.-lactone can be efficiently produced at high yield.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: December 7, 1999
    Assignee: Takasago International Corporation
    Inventors: Sotaro Miyano, Tetsutaro Hattori, Yutaka Suzuki, Shuichi Oi, Takashi Miura, Tsutomu Hashimoto
  • Patent number: 5981771
    Abstract: The present invention provides a catalyst which exhibits a high catalytic activity and allows asymmetric reaction in a high asymmetric yield to obtain a reaction product having a high optical purity. The present invention also provides a process for the preparation of an optically active 4-methyl-2-oxetanone having a high optical purity useful as starting material of polymer in a high yield in a short period in the presence of the foregoing catalyst. A novel ruthenium-iodo-optically active phosphine complex is provided, represented by the following general formula (1):Ru--I.sub.2 -(R.sup.1 -BINAP) (1)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by the following general formula (2): ##STR1## wherein R.sup.1 represents an aryl group which may have a substituent selected from the group consisting of a C.sub.1-4 lower alkyl group, a C.sub.1-4 lower alkoxy group, a C.sub.1-4 lower alkylamino group, and a halogen atom or a C.sub.3-8 cycloalkyl group.
    Type: Grant
    Filed: June 22, 1998
    Date of Patent: November 9, 1999
    Assignee: Takasago International Corporation
    Inventors: Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
  • Patent number: 5725731
    Abstract: A sizing composition for fine paper that does not encounter machine feed problems in high-speed converting or reprographic operations is not solid at 35.degree. C. and comprises a mixture of 2-oxetanone compounds that are the reaction product of a reaction mixture comprising (a) a feedstock comprising primarily unsaturated fatty acids and (b) a feedstock comprising primarily saturated fatty acids, or acid halides thereof, provided that at least 20 mole % of the reaction mixture fatty acids comprise saturated fatty acids and at least 20 mole % of the reaction mixture fatty acids comprise unsaturated fatty acids.
    Type: Grant
    Filed: May 8, 1995
    Date of Patent: March 10, 1998
    Assignee: Hercules Incorporated
    Inventors: Clement L. Brungardt, John C. Gast, Jian-Jian Zhang
  • Patent number: 5672721
    Abstract: A process for the preparation of low-solvent alkyl diketenes of the general formula: ##STR1## in which R.sup.1 denotes C.sub.10 -C.sub.30 alkyl or C.sub.10 -C.sub.30 alkenyl andR.sup.2 denotes hydrogen or C.sub.1 -C.sub.8 alkyl, by causing carboxylic chlorides of the formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings, to react with tertiary amines of the formula III ##STR3## in which R.sup.3, R.sup.4, R.sup.5 denote C.sub.1 -C.sub.12 alkyl or C.sub.3 -C.sub.12 cycloalkyl andR.sup.3 and R.sup.4 together denote a C.sub.2 -C.sub.11 alkylene dichain optionally interrupted by oxygen or nitrogen,in a substantially water-immiscible, inert solvent, wherein distillation is carried out at temperatures ranging from 80.degree. to 130.degree. C. and pressures ranging from 10 to 500 mbar and subsequently with the addition of water or steam.
    Type: Grant
    Filed: April 26, 1996
    Date of Patent: September 30, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Ettl, Wolfgang Kasel, Matthias Fankhanel, Wolfgang Reuther
  • Patent number: 5530145
    Abstract: Novel anticholesteremic compounds capable of reducing blood cholesterol levels. Also included in this invention are (i) intermediates from which the abovementioned anticholesteremic compounds can be prepared, and (ii) methods for preparing both the intermediates and the anticholesteremic compounds.
    Type: Grant
    Filed: December 6, 1994
    Date of Patent: June 25, 1996
    Assignee: Syn-Tech Chem & Pharm Co., Ltd.
    Inventors: Hui-Po Wang, On Lee, Chin-Tsai Fan
  • Patent number: 5525738
    Abstract: A process is disclosed for the synthesis of alkyl ketene dimers by the dehydrohalogenation of a C.sub.8 -C.sub.22 saturated or unsaturated linear fatty acid halide, comprising reacting the fatty acid chloride with a cyclic tertiary amine in a solvent that is selected from the group consisting of cycloalkanes and alkanes at a temperature of up to 75.degree., mechanically separating tertiary amine hydrochloride salts from alkyl ketene dimer dissolved in the solvent, and recovering the alkyl ketene dimer from the solvent.
    Type: Grant
    Filed: March 24, 1994
    Date of Patent: June 11, 1996
    Assignee: Hercules Incorporated
    Inventor: Jian J. Zhang
  • Patent number: 5502218
    Abstract: A process for the production of ketene dimers from fatty acid halides by reaction with tertiary amines. The process is operated batchwise and the reaction is started in the presence of an initial reaction mixture containing ketene dimer and pre-prepared crystals of tertiary amine hydrogen halide and is carried out in the substantial absence of additional solvents.
    Type: Grant
    Filed: September 15, 1994
    Date of Patent: March 26, 1996
    Assignee: Eka Nobel AB
    Inventors: John F. Nicholass, Piotr Zettinger
  • Patent number: 5484952
    Abstract: A process for making an alkyl ketene dimer by the dehydrohalogenation reaction of a C.sub.8 -C.sub.32 aliphatic fatty acid chloride with a tertiary amine in an inert solvent and the product of the process; the solvent comprising at an oxygenated hydrocarbon.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: January 16, 1996
    Assignee: Hercules Incorporated
    Inventors: Timothy F. Nolan, Brian M. Stubbs
  • Patent number: 5412112
    Abstract: Novel 3-substituted derivatives of 2,2-dimethyl-5-substituted phenoxy-pentanoic acids of formula (I) are prepared. These compouds are prepared from 2,2-dimethyl-5-substituted phenoxy-3-hydroxy-pentanoic acid-.beta.-lactones (formula II). The .beta.-lactones are prepared by condensing relevant phenoxypropanals with dimethylketene.
    Type: Grant
    Filed: June 14, 1994
    Date of Patent: May 2, 1995
    Assignee: Industrial Technology Research Institute
    Inventors: Hui-Po Wang, On Lee, Chin-Tsai Fan
  • Patent number: 5370774
    Abstract: The invention relates to a process for isolating pure diketene with recovery of materials of value by continuous, two-stage distillation of crude diketene at reduced pressure and with continuous reaction of the resulting distillation residue with acetic acid, pure diketene and acetic anhydride being separated off by means of the two-stage distillation. In the stabilization of the distillation residue with acetic acid, reutilizable acetic acid, which contains acetone with or without acetic anhydride, is recovered.
    Type: Grant
    Filed: November 3, 1993
    Date of Patent: December 6, 1994
    Assignee: Wacker-Chemie GmbH
    Inventors: Gerhard Kuenstle, Alois Maier
  • Patent number: 5344943
    Abstract: Long-chain ketene dimers are prepared in a process in which in the absence of an organic solvent, carboxylic acid chloride is fed, with intensive mixing, into a recipient of triethyl amine at a rate of not more than 3 moles/hour per mole of present triethyl amine, and the mixing rate, feed rate, and heat exchange are so attuned to each other that the viscosity of the mixture always is less than 250 mPa.s, measured at 60.degree. C. (rate of shear higher than 100 l/sec). The process is characterized in that the molar ratio of the total amount of carboxylic acid chloride fed in to the recipient amount of amine is 1:1.025 to 1:2, and, after the conversion, the reaction mixture containing the ketene dimer is treated with diluted aqueous hydrochloric acid or an aqueous solution of triethyl amine hydrochloride and hydrochloric acid, and the ketene dimer is separated. The ketenes prepared in accordance with the present invention are highly suitable for use in paper sizing.
    Type: Grant
    Filed: December 29, 1992
    Date of Patent: September 6, 1994
    Assignee: Akzo Nobel N.V.
    Inventor: Nils Brolund
  • Patent number: 5252754
    Abstract: Aldoketene dimer sizing agents that can efficiently impart both oil and water sizing properties to paper, of an unsaturated .beta.-lactone structure containing terminal perfluoralkyl groups separated from the ketene moiety by at least three carbon atoms, which may be attached to a halogen other than fluorine or an ether, thioether, amide, tertiary amine, ester, or side chain functionality.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: October 12, 1993
    Assignee: Hercules Incorporated
    Inventor: Kyle J. Bottorff
  • Patent number: 4999438
    Abstract: The polymer portion in the production of diketene by the dimerization of ketene obtained from acetic acid by pyrolysis is reduced by the addition of sulfur dioxide to the ketene gas or to the reaction medium.
    Type: Grant
    Filed: January 3, 1990
    Date of Patent: March 12, 1991
    Assignee: Lonza Ltd.
    Inventors: Renzo Bergmin, Wilhelm Quittmann, Josef Stoffel
  • Patent number: 4808735
    Abstract: Process for the reduction of the ketene trimer portion in raw diketene by mixing of the diketene with water, an alcohol, a phenol or a carboxylic acid, and heating the mixture to 50.degree. to 130.degree. C., and then distilling off the diketene.
    Type: Grant
    Filed: April 5, 1988
    Date of Patent: February 28, 1989
    Assignee: Lonza Ltd.
    Inventors: Renzo Bergamin, Wilhelm Quittmann
  • Patent number: 4621146
    Abstract: Compounds of the formula ##STR1## and their preparation wherein R.sup.1 and R.sup.2 are each selected from H and alkyl wherein the alkyl moieties are straight or branched chain of 1-20 carbons, preferably 1-6 carbons. Readily prepared therefrom are the corresponding unsaturated esters of the formula R.sup.2 S(R.sup.1)CH--CH.sub.2 --CH.dbd.CH--COO-alkyl which are useful as intermediates in the preparation of herbicides.
    Type: Grant
    Filed: December 20, 1985
    Date of Patent: November 4, 1986
    Assignee: Eastman Kodak Company
    Inventor: John A. Hyatt
  • Patent number: 4472589
    Abstract: The new compound 4-chloro-4-chloromethyloxetan-2-one can be prepared by reacting diketene with sulphuryl chloride under conditions in which free radicals are formed.The 4-chloro-4-chloromethyloxetan-2-one exhibits antimicrobial activity. It is also useful as an intermediate, for example for the production of pigments and dyestuffs.
    Type: Grant
    Filed: February 25, 1983
    Date of Patent: September 18, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Brian Tuck
  • Patent number: 4398033
    Abstract: The new compound 4-chloro-4-chloromethyloxetan-2-one can be prepared by reacting diketene with sulphuryl chloride under conditions in which free radicals are formed.The 4-chloro-4-chloromethyloxetan-2-one exhibits antimicrobial activity. It is also useful as an intermediate, for example for the production of pigments and dyestuffs.
    Type: Grant
    Filed: March 8, 1982
    Date of Patent: August 9, 1983
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Brian Tuck
  • Patent number: 4363923
    Abstract: Novel compounds having the formula I ##STR1## are described wherein X is a chlorine, bromine or iodine atom and Y is a residue having the formula R.sup.1 R.sup.2 R.sup.3 C- wherein R.sup.1 and R.sup.2 are the same or different and each is a fluorine, chlorine or bromine atom and R.sup.3 is a hydrogen, fluorine, chlorine or bromine atom, a group -CR.sup.4 R.sup.5 R.sup.6, a cyano group, a group-COR.sup.7 or -PO(R.sup.8).sub.2 wherein R.sup.4, R.sup.5, R.sup.6, independently, are F, Cl or Br, R.sup.7 nd R.sup.8 are the same or different and each is a chlorine atom or a group -OR.sup.9 wherein R.sup.9 is a C.sub.1 -C.sub.4 straight chain or branched alkyl group with the proviso that when X is a chlorine atom, none of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6, can be a bromine atom.They can be obtained by reacting diketene with a compound XY in the presence of an agent capable of forming free radicals. Compounds (I) have biocidal activity against various organisms, e.g. bacteria, fungi and algae.
    Type: Grant
    Filed: March 27, 1981
    Date of Patent: December 14, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: John G. Dingwall, Brian Tuck
  • Patent number: 4361563
    Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen; trifluoromethyl; alkyl of 1 to 11 carbon atoms; cycloalkyl of 3 to 7 carbon atoms; hydroxyl; alkoxy of 1 to 6 carbon atoms; mercapto; (alkyl of 1 to 6 carbon atoms)-mercapto; phenyl-(alkyl of 1 to 3 carbon atoms); phenyl; or mono-, di- or tri-substituted phenyl, where the substituents, which may be identical to or different from each other, are each halogen, alkyl of 1 to 4 carbon atoms, (alkyl of 1 to 6 carbon atoms)-sulfinyl, hydroxyl, alkoxy of 1 to 6 carbon atoms, mercapto or (alkyl of 1 to 6 carbon atoms)-mercapto;R.sub.2 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or phenyl-(alkyl of 1 to 3 carbon atoms); andR.sub.3 is alkyl of 1 to 6 carbon atoms; optically active antipodes thereof; and non-toxic, pharmaceutically acceptable acid addition salts of said compounds or of said optically active antiposed. The compounds are useful as cardiotonics and antithrombotics.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: November 30, 1982
    Assignee: Dr. Karl Thomae Gesellschaft mit Beschrankter Haftung
    Inventors: Volkhard Austel, Joachim Heider, Wolfgang Eberlein, Willi Diederen, Walter Haarmann