Nitrogen Attached Indirectly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/402)
  • Patent number: 5210193
    Abstract: 7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: May 11, 1993
    Assignee: American Cyanamid Company
    Inventors: Phaik-Eng Sum, Joseph P. Joseph, Carl B. Ziegler, Jr., Daniel B. Moran, Yang-I Lin
  • Patent number: 5202490
    Abstract: A continuously generated alkyleneamines producers composition comprising based on 100% of the moles of the compostion and exclusive of any MEA and water present,a) about 15 to about 35 mole % DETA,b) about 15 to about 55 mole % EDA (net generated),c) about 10 to about 35 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines, andg) a DETA to AEEA mole ratio greater than about 0.77 to less than 1.35,and the process of producing the same, which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 10 to about 50 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5202491
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 20 to about 40 mole % DETA,b) about 15 to about 60 mole % EDA (net generated),c) about 5 to about 18 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) less than about 1 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a DETA to AEEA mole ratio greater than about 1.35, andh) an EDA to DETA mole ratio less than 2.60,and the process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is greater than 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5200520
    Abstract: A process for the production of piperazinylpyrimidine derivatives of the formula I: ##STR1## wherein R.sub.1 is a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group, branched or unbranched. In the process, piperazine or its hydrate is acid-converted with cyanamide to an amidine salt and the latter is then reacted with a carbonyl compound in the presence of a base to the end product.
    Type: Grant
    Filed: December 10, 1991
    Date of Patent: April 6, 1993
    Assignee: Lonza Ltd.
    Inventor: David L. Kuo
  • Patent number: 5196588
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 14 to about 20 mole % DETA,b) about 45 to about 75 mole % EDA (net generated),c) about 4 to about 10 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 0.5 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polymines,g) an EDA to DETA mole ratio greater than about 2.60,h) a DETA to AEEA mole ratio greater than about 1.35, andi) an EDA to AEEA mole ratio greater than about 8,and a process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: March 23, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5166442
    Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.
    Type: Grant
    Filed: July 16, 1991
    Date of Patent: November 24, 1992
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5166415
    Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA and AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: November 24, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
  • Patent number: 5164397
    Abstract: A compound of formula (I) ##STR1## in which n denotes 2, 3, 4, or 5,p denotes 0 or 1,m denotes 0, 1, 2, 3, 4, or 5, andR.sub.1 denotes a hydrogen atom or a methyl group,each X, which may be identical or different to any other X if m is greater than 1, denotes fluorine, chlorine, methoxy, isopropyl or cyclopropyl,in the form of a free base or an acid addition salt.
    Type: Grant
    Filed: December 27, 1990
    Date of Patent: November 17, 1992
    Assignee: Synthelabo
    Inventors: Pascal George, Philippe Manoury, Jacques Froissant, Jean-Pierre Merly
  • Patent number: 5142089
    Abstract: Dye corresponding to the following formula - ##STR1## wherein Z represents CN, COOR.sup.1 or CONR.sup.2 R.sup.3 ;R.sup.1, R.sup.2 and R.sup.3 each independently represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or R.sup.2 and R.sup.3 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus;Y represents OR.sup.4 or NR.sup.5 R.sup.6 or CN;R.sup.4 represents hydrogen, substituted or unsubstituted or unsubstituted aryl, SO.sub.2 R.sup.7, COR.sup.7, CSR.sup.7, POR.sup.7 R.sup.8 ;R.sup.5 and R.sup.6 each independently has one of the significances given to R.sup.4 or represents substituted or unsubstituted amino, or R.sup.5 and R.sup.6 together represent the necessary atoms to close a heterocyclic nucleus or substituted heterocyclic nucleus, including a heterocyclic nucleus with an aliphatic or aromatic ring fused-on;R.sup.7 and R.sup.
    Type: Grant
    Filed: June 4, 1991
    Date of Patent: August 25, 1992
    Assignee: Agfa-Gevaert, N.V.
    Inventor: Luc J. Vanmaele
  • Patent number: 5134236
    Abstract: Novel 1-phenyl-3-(1-piperazinyl)-1H-indazoles, intermediates and processes for the preparation thereof, and methods for alleviating pain, treating convulsions, and treating depression utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: July 28, 1992
    Assignee: Hoechst-Roussel Pharmaceuticals Incorporated
    Inventor: Joseph T. Strupczewski
  • Patent number: 5118850
    Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxdies, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.
    Type: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5105013
    Abstract: A process for the preparation of permethylated amines, particularly pentamethyldiethylenetriamine, by the reductive methylation of diethylenetriamine in the presence of hydrogen, a nickel-containing catalyst, aqueous formaldehyde and methanol, comprising feeding continuously the formalehyde to the reaction system in two phases. In the first phase, a sufficient amount of formaldehyde to mono-methylate the primary amine groups present, is fed to the reaction system at a high flow rate, and thereafter the flow rate of the formaldehyde is substantially reduced, for the reductive methylation of the secondary amine groups. By this method the production of by-products is substantially reduced and preparation times are significantly shorter in comparison to processes where the formaldehyde flow rate remains constantly high for the entirety of the reaction.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Maarten Tanis, Govind Rauniyar
  • Patent number: 5091583
    Abstract: The invention pertains to tertiary amines used as catalysts for the preparation of polyurethane foams prepared via the catalytic reaction of a polyisocyanate with a polyol in the presence of blowing agents, etc. The tertiary amine catalysts are prepared by reacting an olefinic nitrile with aliphatic polyol having at least secondary hydroxyl functionality in a ratio less than stoichiometric for providing cyanoalkylated polyol having residual hydroxyl functionality. The resulting cyanoalkylated polyol then is reacted with a secondary amine under conditions for effective reductive alkylation.The tertiary amine catalysts, because of residual secondary hydroxyl functionality, provide for uniform dispersion within a polyurethane, formulation; they provude for additional or extended pot life in polyurethane formulations at temperature below reaction condition, and they are bound by reaction on cure.
    Type: Grant
    Filed: May 9, 1991
    Date of Patent: February 25, 1992
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Richard V. C. Carr, George J. Wasilczyk, Robert G. Petrella
  • Patent number: 5073635
    Abstract: A process of preparing linearly-extended polyalkylenepolyamines, such as linear and branched polyethylenepolyamines, comprising contacting a difunctional aliphatic alcohol, such as monoethanolamine, with a reactant aliphatic amine, such as ethylenediamine, in the presence of a metal silicate catalyst wherein the metal is selected from Groups IIIB, IVB, VB and the lanthanide rare earth metals. Reactions of piperazines with alkanolamines to yield alcohol-extended and/or amine-extended piperazines are included in the process of this invention.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5070202
    Abstract: A process for the production of alkylaminonitriles by reacting 2-pentenenitrile and an alkylamine in the presence of 15 to 60% by weight water.
    Type: Grant
    Filed: March 28, 1990
    Date of Patent: December 3, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank E. Herkes
  • Patent number: 5068330
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 15 to about 50 mole % AEEA,b) about 15 to about 55 mole % EDA,c) about 10 to about 20 mole % DETA,d) about 5 to about 20 mole % of the combination of PIP,AEP and HEP,3) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) an DETA to AEEA mole ratio less than 0.77, andh) an EDA to AEEA mole ratio less than 8;and a process of manufacturing the same, which comprises feeding hydrogen, ammonia and MEA to a reaction zone containing a fixed bed of a reductive amination catalyst, wherein the hydrogen comprises about 20 to about 60 mole percent of the feed in the reaction zone and the mole ratio of ammonia to MEA is about 1 to about 5, the temperature of the reaction zone is about 120.degree. C. to about 300.degree. C.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5068329
    Abstract: A continuously generated alkyleneamines produces composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 50 to about 90 mole % AEEA,b) less than about 3 mole % EDA but more than 0.01 mole % EDA,c) less than about 2 mole % DETA but more than 0.01 mole % DETA,d) about 5 to about 18 mole % of the combination of PIP, AEP and HEP,e) about 5 to about 20 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a mole ratio of AEEA to the combination of PIP, AEP, HEP, DETA and EDA is greater than about 2.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5059391
    Abstract: It has been found out that polyaralkylamines of the formula stated in the claims are useful as corrosion inhibitors for metallic materials; furthermore were found out new polyaralkylamines of the formula stated in the claims and a process for their preparation.
    Type: Grant
    Filed: September 1, 1988
    Date of Patent: October 22, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Christian Wegner, Heinz-Joachim Rother
  • Patent number: 5047570
    Abstract: 3-Amino-2-cyanoacrylonitrile derivatives of the formula ##STR1## where R is substituted C.sub.1 -C.sub.10 -alkyl, substituted or unsubstituted styryl, substituted or unsubstituted phenyl or aromatic heterocyclyl, are prepared by treating a nitrile in an inert organic diluent at from 0.degree. to +30.degree. C. with a substituted or unsubstituted C.sub.1 -C.sub.6 -alkanol in the presence of a hydrogen halide and reacting the resulting iminoester hydrohalide directly or after isolation with malodinitrile in an inert organic diluent at from 20.degree. to 100.degree. C. in the presence of a base.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: September 10, 1991
    Assignee: BASF Aktiengesellschaft
    Inventor: Ernst Schefczik
  • Patent number: 5032598
    Abstract: Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members and Q is a nitrogen containing heterocycle, are antiarrhythmic agents.
    Type: Grant
    Filed: December 8, 1989
    Date of Patent: July 16, 1991
    Assignee: Merck & Co., Inc.
    Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
  • Patent number: 5026853
    Abstract: A method of improving sleep in warm-blooded animals suffering from sleep disorders, which method comprises the administration of particular N-aryl-piperazinealkanamide derivatives and compositions containing the same. Novel N-aryl-piperazinealkanamide derivatives.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: June 25, 1991
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Marc G. C. Verdonck
  • Patent number: 5011999
    Abstract: A process for the preparation of predominantly non-cyclic polyalkylenepolyamines comprising contacting a difunctional aliphatic alcohol with ammonia or a primary or secondary aliphatic amine in the presence of a catalyst selected from the group consisting of Group VB metal oxides, niobium phosphates, tantalum phosphates, and mixtures thereof. For example, monoethanolamine is aminated by ethylenediamine to predominantly linear and branched polyethylenepolyamines in the presence of a catalyst containing niobium oxide supported on boehmite alumina.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: April 30, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
  • Patent number: 4999356
    Abstract: Novel 1-phenyl-3-(1-piperazinyl)-1H-indazoles, intermediates and processes for the preparation thereof, and methods for alleviating pain, treating convulsions, and treating depression utilizing compounds or compositions thereof are disclosed.
    Type: Grant
    Filed: December 23, 1988
    Date of Patent: March 12, 1991
    Assignee: Hoechst-Roussel Pharmaceuticals, Inc.
    Inventor: Joseph T. Strupczewski
  • Patent number: 4996363
    Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.
    Type: Grant
    Filed: December 20, 1988
    Date of Patent: February 26, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 4990672
    Abstract: This invention relates to propylene-linked polyethylene polyamines and a process for preparing such propylene-linked polyethylene polyamines. These propylene-linked polyethylene polyamines are characterized as having high molecular weight and the amine value is distributed over a wide range of primary, secondary, and tertiary amine functionality.The propylene-linked polyethylene polyamines are prepared by reacting a polyamine containing an ethylene amine functionality with acrylonitrile or methacrylonitrile to form a cyanoethylated polyamine containing the ethylene linkage and then reductively alkylating the resulting cyanoethylated derivative in the presence of a polyamine containing an ethylene linkage. Typically, a polyethylene polyamine such as diethylenetriamine or triethylene tetramine is reacted with acrylonitrile and then hydrogenated under reductive alkylation conditions.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: February 5, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Thomas A. Johnson, Ismail O. Abdalmuhdi
  • Patent number: 4983735
    Abstract: A process for preparing alcohol-extended and amine-extended piperazines comprising contacting a difunctional aliphatic alcohol with a reactant amine, wherein at least one of the aliphatic alcohol or the reactant amine contains a piperazine moiety, in the presence of a catalyst containing a tungsten heteropoly acid. For example, monoethanolamine reacts with piperazine in the presence of a 12-tungstophosphoric acid catalyst to yield predominantly N-(2-aminoethyl)piperazine, which is an amine-extended piperazine.
    Type: Grant
    Filed: July 20, 1988
    Date of Patent: January 8, 1991
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 4983736
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: January 8, 1991
    Assignee: Union Carbide Chemicals and Plastic Company Inc.
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 4981965
    Abstract: A base precursor in the form of a salt of an organic base with a carboxylic acid is disclosed. The organic base is a diacidic to tetraacidic base which is composed of two to four guanidine moieties and at least one linking group for the guanidine moities. The organic base is such a hydrophilic compound that the number of carbon atoms contained in the organic base is not more than six times the number of the guanidine moieties. The linking group is a residue of a hydrocarbon or a heterocyclic ring. The guanidine moiety corresponds to an atomic group formed by removing one or two hydrogen atoms from a compound having the following formula (I): ##STR1## where each of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 independently is hydrogen, an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, an aralkyl group, an aryl group or a heterocyclic group, each of which may have one or more substituent groups, and any two of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 1, 1991
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yoshiharu Yabuki, Jiro Tsukahara, Taku Nakamura
  • Patent number: 4977266
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,(a) about 15 to about 50 mole % AEEA,(b) about 15 to about 55 mole % EDA,(c) about 10 to about 20 mole % DETA,(d) about 5 to about 20 mole % of the combination of PIP, AEP and HEP,(e) about 3 to about 10 mole % of one or more of TETAs and TEPAs,(f) less than about 1 mole % of other polyalkylene polyamines,(g) an DETA to AEEA mole ratio less than 0.77, and(h) an EDA to AEEA mole ratio less than 8;and a process of manufacturing the same, which comprises feeding hydrogen, ammonia and MEA to a reaction zone containing a fixed bed of a reductive amination catalyst, wherein the hydrogen comprises about 20 to about 60 mole percent of the feed in the reaction zone and the mole ratio of ammonia to MEA is about 1 to about 5, the temperature of the reaction zone is about 120.degree. C. to about 300.degree. C.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: December 11, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 4973692
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,(a) about 50 to about 90 mole % AEEA,(b) less than about 3 mole % EDA but more than 0.01 mole % EDA,(c) less than about 2 mole % DETA but more than 0.01 mole % DETA,(d) about 5 to about 18 mole % of the combination of PIP, AEP and HEP,(e) about 5 to about 20 mole % of one or more of TETAs and TEPAs,(f) less than about 1 mole % of other polyalkylene polyamines,(g) a mole ratio of AEEA to the combination of PIP, AEP, HEP, DETA and EDA is greater than about 2.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: November 27, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 4968679
    Abstract: New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.
    Type: Grant
    Filed: May 22, 1989
    Date of Patent: November 6, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber, George S. Allen
  • Patent number: 4945177
    Abstract: Novel 2,2-dibromo-3-oxonitriles of Formula I,R--CO--CBr.sub.2 --CN (I)in which R represents in each case a possibly substituted or unsubstituted aliphatic, cycloaliphatic, aromatic or heterocyclic group, with the exception of a phenyl group substituted with 1 to 3 chlorine atoms, can be obtained in that a carboxylic acid ester of Formula IIR--CO--OR' (II)in which R has the significance indicated for Formula I, and in which R' represents a straight chain or branched alkyl group with 1 to 4 carbon atoms, is reacted with acetonitrile in the presence of a strong base, the 3-oxonitrile produced is isolated from the reaction mixture and reacted in a solvent inert with respect to bromine and in the presence of a hydrogen bromide acceptor, possibly under cooling, and the 2,2-dibromo-3-oxonitrile of Formula I obtained is isolated from the reaction mixture.
    Type: Grant
    Filed: December 23, 1986
    Date of Patent: July 31, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Horst-Juergen Krause, Hans-Theo Leinen, Rudolf Lehmann
  • Patent number: 4922024
    Abstract: A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: May 1, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
  • Patent number: 4906634
    Abstract: Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as cardiovascular agents, especially as antiarrhythmic agents are described. Pharmaceutical formulations containing such compounds are also discussed.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: March 6, 1990
    Assignee: Schering A.G.
    Inventors: Stanley S. Greenberg, William C. Lumma, Jr., Klaus Nickisch, Ronald A. Wohl
  • Patent number: 4906782
    Abstract: Ammonia and/or an alkyleneamine is reacted with an alkanolamine by using a miobium-containing substance as a catalyst to obtain an alkyleneamine having an increased number of alkylene units. The niobium-containing substance has a high activity and a high heat resistance, and is not or only slightly soluble in the water-containing reaction liquid.
    Type: Grant
    Filed: August 12, 1987
    Date of Patent: March 6, 1990
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Yasushi Hara, Sadakatsu Kumoi, Yukihiro Tsutsumi
  • Patent number: 4888355
    Abstract: A compound selected from the group consisting of all enantiomeric and diastereoisomeric forms possible of compounds of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, halogen, and alkyl and alkoxy of 1 to 5 carbon atoms, R.sub.1 and R.sub.2 are individually selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, one of A and B being ##STR2## and the other being ##STR3## R is hydrogen or alkyl of 1 to 5 carbon atoms, Z is --(CH.sub.2).sub.n -- or branched alkylene of 2 to 8 carbon atoms, n is an integer from 0 to 5, Y is selected from the group consisting of naphthyl, indenyl, heterobicyclics and heteromonocyclic containing 5 to 6 ring members, all optionally substituted with at least one member of the group consisting of alkyl and alkoxy of 1 to 5 carbon atoms, halogen, --OH, --CF.sub.3, --NO.sub.2, --NH.sub.
    Type: Grant
    Filed: December 22, 1987
    Date of Patent: December 19, 1989
    Assignee: Roussel Uclaf
    Inventors: Francois Clemence, Odile Le Martret, Michel Fortin, Francoise Delevallee
  • Patent number: 4888425
    Abstract: Enhanced production of predominantly linearly extended polyalkylene polyamines from alkylenediamines reacted with alkylene glycols or alkanolamines using a phosphorus-containing catalyst is achieved by removing water during the reaction.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: December 19, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: William B. Herdle
  • Patent number: 4883797
    Abstract: Derivatives of piperazine having the general formula ##STR1## wherein R.sub.1 is benzhydryl or cinnamyl and R.sub.2 is selected from the group consisting of ##STR2## --(CH.sub.2).sub.3 --R.sub.8, --CH.sub.2 NHR.sub.9, --CH.sub.2 NH.sub.2 and --COR.sub.10 ; wherein R.sub.3 is hydrogen, chloromethyl, (4-benzhydryl-1-piperazinyl) methyl, 4-morpholinylmethyl or 1-piperidinylmethyl, R.sub.4 is hydrogen, chloromethyl or carbethoxy, R.sub.5 and R.sub.6 taken together are an oxygen atom or the radical --O--(CH.sub.2).sub.2 --O--, R.sub.7 is methyl, phenyl or 2-thienyl, R.sub.8 is 4-morpholinyl, 1-piperidinyl or 4-benzhydryl-1-piperazinyl, R.sub.9 is 2-oxo-1- (pyrrolidinyl) acetyl, 2-hydroxybenzoyl or 4-sulfamoylbenzoyl, R.sub.10 is 2-oxo-1-(pyrrolidinyl)methyl or 4-sulfamoylphenyl and X is oxygen or NH; as well as methods for making the same and their use in a pharmaceutical composition is proposed. The compounds have cardiovascular properties and increasing effects on cerebral flow.
    Type: Grant
    Filed: January 7, 1988
    Date of Patent: November 28, 1989
    Assignee: Ferrer Internacional, S.A.
    Inventors: Rafael Foguet, Jose A. Ortiz, Santiago Gubert, Manuel M. Raga, Aurelio Sacristan
  • Patent number: 4880808
    Abstract: A method of improving sleep in warm-blooded animals suffering from sleep disorders, which method comprises the administration of particular N-aryl-piperazinealkanamide derivatives and compositions containing the same. Novel N-aryl-piperazinealkanamide derivatives.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: November 14, 1989
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Marc G. C. Verdonck
  • Patent number: 4877879
    Abstract: In an improved process for the preparation of polyether compositions, amine-initiated, alkaline catalyzed polyethers are neutralized with a substantial excess of formic acid that neutralizes the catalyst and stabilizes the resultant composition. This is particularly advantageous where tertiary nitrogen is found in the amine initiator or in the polyether that results.
    Type: Grant
    Filed: January 4, 1988
    Date of Patent: October 31, 1989
    Assignee: Dow Chemical (Nederland) B.V.
    Inventor: Michael A. P. Gansow
  • Patent number: 4873262
    Abstract: New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 10, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber, George S. Allen
  • Patent number: 4845297
    Abstract: Process for producing polyamines by a catalytic reduction reaction of a cyanoethylated N-(2-aminoethyl)piperazine and cyanoethylated compounds of polyamines containing 4 or more amino groups in the molecule.
    Type: Grant
    Filed: December 30, 1987
    Date of Patent: July 4, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
  • Patent number: 4837323
    Abstract: The reaction product of an .alpha.,.beta.-ethylenically unsaturated aldehyde with an organic amine further reacted with a carboxylic acid, organic halide or an epoxide containing compound is employed as corrosion inhibitors in a process for preventing corrosion of ferrous metals in contact with corrosive brine, oil and gas well fluids.
    Type: Grant
    Filed: May 13, 1987
    Date of Patent: June 6, 1989
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Martinez, Duane S. Treybig, Terry W. Glass
  • Patent number: 4831034
    Abstract: Compounds of formula (I) in which the broken line forms a phenyl, naphthyl, pyridyl, indolizine, pyrrolo[1,2-a]pyrazine, pyrrolo[1,2-a]pyrimidine or pyrrolo[1,2-c]pyrimidine ring-system, R=H, halogen, OH, alkyl, alkyloxy or alkylthio, R'=H, halogen, alkyl, alkyloxy, alkylthio, CN or CF.sub.3, n and p=1, 2 or 3, the alkyl radicals having 1 to 4 C in a straight or branched chain.These products are useful as neuroleptics.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: May 16, 1989
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Barreau, Marie-Therese Comte, Jean-Luc Malleron, Gerard Ponsinet
  • Patent number: 4816576
    Abstract: The invention relates to a sulphonic acid amidamine corresponding to the following general formula I: ##STR1## wherein R.sup.1 represents a C.sub.8 -C.sub.30 linear, saturated aliphatic hydrocarbon group or said group which is substituted by one or more chlorine atoms;R.sup.2 and R.sup.5 independently represent hydrogen or C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkyl which is substituted with one of the groups: hydroxyl, amino, mercapto, cyano, carboxyl or carbamoyl, and/or is interrupted by at least one oxy (--O--) or thio (--S--) group;R.sup.3 and R.sup.4 independently represent C.sub.2 -C.sub.13 alkylene or C.sub.5 -C.sub.7 cycloalkylene or said alkylene or cycloalkylene groups which are substituted with one of the groups: hydroxyl, amino, mercapto, cyano, carboxyl or carbamoyl;p represents zero or an integer of from 1 to 3;q represents zero or an integer of from 1 to 12; andn represents an integer of from 1 to 8.
    Type: Grant
    Filed: June 23, 1986
    Date of Patent: March 28, 1989
    Assignee: Bayer Akteingesellschaft
    Inventors: Hans-Josef Buysch, Wolfgang Wellner, Hermann Gruber
  • Patent number: 4749701
    Abstract: Disclosed are an aminostyryl compound represented by Formula I: ##STR1## wherein A represents a linking group having 3 to 4 chain members; B represents an unsubstituted or substituted 5 to 6-membered monocyclic type heterocyclic residue containing 1 to 2 hetero atoms, an unsubstituted or substituted condensed heterocyclic residue which contains 5 to 6-membered monocyclic type heterocycle containing 1 to 2 hetero atoms, a naphthyl group or an alkyl group having 5 to 7 carbon atoms,a composition having leukotriene antagonism which contains an aminostyryl compound represented by Formula I as the effective ingredient, and a method of antagonizing SRS based on leukotriene antagonistic activity by employing the same.
    Type: Grant
    Filed: December 15, 1986
    Date of Patent: June 7, 1988
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Yoshio Hayashi, Tomei Oguri, Masaki Shinoda, Kazuo Takahashi
  • Patent number: 4725681
    Abstract: An ethanolamine, preferably diethanolamine, is converted to triethylenediamine or 1,4-bis(2-hydroxyethyl)piperazine, or both by pyrolysis using a B-subgroup metal oxide such as titanium dioxide or zirconium dioxide, as catalyst. In addition it has also been discovered that 1,4-bis(2-hydroxyethyl)piperazine and N-(2-hydroxyethyl)piperazine can be converted in high yields and conversions into triethylenediamine by pyrolysis using the same type of catalyst. When using an ethanolamine as the feedstock and a Group IV-B metal oxide as the catalyst, the process usually results in the coproduction of triethylenediamine and 1,4-bis(2-hydroxyethyl)piperazine, and the latter can be recovered and used as a raw material for the production of additional triethylenediamine, as by recycle to the same reactor or as feedstock to an additional pyrolysis reactor.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: February 16, 1988
    Assignee: Ethyl Corporation
    Inventors: Ronald L. Shubkin, Duane C. Hargis
  • Patent number: 4709032
    Abstract: This invention relates to novel isoquinolinesulfonamide derivatives of Formula (I): ##STR1## wherein A is a C.sub.0-10 alkylene group or a C.sub.0-10 alkylene group having a C.sub.1-10 alkyl group, a phenyl group, a substituted phenyl group or a phenylalkyl group; R.sub.1 and R.sub.2 each is a hydrogen atom; or R.sub.1 and R.sub.2 are linked directly to form an ethylene group unsubstituted or substituted with a C.sub.1-4 alkyl group;R.sub.3 and R.sub.4 each is a hydrogen atom, a C.sub.1-6 alkyl group or linked directly to form a C.sub.2-6 alkylene group; and the pharmaceutically acceptable acid addition salt thereof, and to a process for preparing them. The isoquinoline derivatives possess a relaxatory action for vascular smooth muscle and action for increasing blood flow and are useful as a vasodilator and a hypotensor.
    Type: Grant
    Filed: October 17, 1986
    Date of Patent: November 24, 1987
    Assignees: Asahi Kasei Kogyo Kabushiki Kaisha, Hiroyoshi Hidaka
    Inventors: Hiroyoshi Hidaka, Takanori Sone
  • Patent number: 4698446
    Abstract: A nitroamine is formed from an aliphatic amine reactant + a nitroalkane + an aldehyde with better conversion, and faster, if the aldehyde is added last, and gradually, so as not to form an alkanolamine intermediate with the aldehyde as in the prior art reactions. In particular, a diamine such as ethylene diamine (EDA) has the unique ability, even among diprimary amines, to react with nitroalkane, to form a salt intermediate to which is added an essentially solvent-free aldehyde such as paraformaldehyde to produce a reaction product consisting essentially of a mixture of (i) a mononitrodialkylenediamine with a disubstituted N-adjacent terminal C atom and (ii) a dinitrotrialkylenediamine with each N-adjacent terminal C atom being disubstituted; and the mixture is obtained in an yield of at least 90 mol %.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: October 6, 1987
    Assignee: The BF Goodrich Company
    Inventors: John T. Lai, Pyong N. Son
  • Patent number: 4670592
    Abstract: A bisbiguanide compound of the formula:R.sup.1 R.sup.2 N.C(:NR.sup.6)NH.C(:NH)NH.CH.sub.2 X-- --(CH.sub.2).sub.3 NH.C(:NH)NH.C(:NR.sup.7)NR.sup.3 R.sup.4 Vor a tautomer thereof, wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which may be the same or different, are each hydrogen, a 1-16C alkyl radical, a 2-16C alkoxyalkyl radical, a 3-12C cycloalkyl radical, a (3-12C cycloalkyl)-(1-4C alkyl) radical, or an optionally substituted phenyl or phenyl(1-4C alkyl) radical, or R.sup.1 and R.sup.2 and the nitrogen atom to which they are attached, or R.sup.3 and R.sup.4 and the nitrogen atom to which they are attached, which may be the same or different, are each a 1-azetidinyl, 1-pyrrolidinyl, piperidino, hexamethyleneimino, heptamethyleneimino, morpholino or 4-(1-8C alkanoyl)-1-piperazinyl radical each of which may bear 1-3C alkyl substituents; each of R.sup.6 and R.sup.7, which may be the same or different, is hydrogen or a 1-8C alkyl radical; and X is a substituted ethylene or ethylidene radical of the formula:--CH.
    Type: Grant
    Filed: May 7, 1984
    Date of Patent: June 2, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Murdoch A. Eakin, Philip N. Edwards, Michael S. Large