Nitrogen Attached Indirectly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/402)
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Patent number: 5210193Abstract: 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: GrantFiled: March 16, 1990Date of Patent: May 11, 1993Assignee: American Cyanamid CompanyInventors: Phaik-Eng Sum, Joseph P. Joseph, Carl B. Ziegler, Jr., Daniel B. Moran, Yang-I Lin
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Patent number: 5202490Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202491Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5200520Abstract: 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: GrantFiled: December 10, 1991Date of Patent: April 6, 1993Assignee: Lonza Ltd.Inventor: David L. Kuo
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Patent number: 5196588Abstract: 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: GrantFiled: May 25, 1990Date of Patent: March 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5166442Abstract: 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: GrantFiled: July 16, 1991Date of Patent: November 24, 1992Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5166415Abstract: 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: GrantFiled: March 30, 1990Date of Patent: November 24, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5164397Abstract: 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: GrantFiled: December 27, 1990Date of Patent: November 17, 1992Assignee: SynthelaboInventors: Pascal George, Philippe Manoury, Jacques Froissant, Jean-Pierre Merly
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Patent number: 5142089Abstract: 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: GrantFiled: June 4, 1991Date of Patent: August 25, 1992Assignee: Agfa-Gevaert, N.V.Inventor: Luc J. Vanmaele
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Patent number: 5134236Abstract: 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: GrantFiled: September 28, 1990Date of Patent: July 28, 1992Assignee: Hoechst-Roussel Pharmaceuticals IncorporatedInventor: Joseph T. Strupczewski
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Patent number: 5118850Abstract: 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: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5105013Abstract: 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: GrantFiled: December 19, 1988Date of Patent: April 14, 1992Assignee: The Dow Chemical CompanyInventors: Maarten Tanis, Govind Rauniyar
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Patent number: 5091583Abstract: 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: GrantFiled: May 9, 1991Date of Patent: February 25, 1992Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Richard V. C. Carr, George J. Wasilczyk, Robert G. Petrella
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Patent number: 5073635Abstract: 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: GrantFiled: June 22, 1990Date of Patent: December 17, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5070202Abstract: 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: GrantFiled: March 28, 1990Date of Patent: December 3, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank E. Herkes
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Patent number: 5068330Abstract: 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: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5068329Abstract: 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: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5059391Abstract: 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: GrantFiled: September 1, 1988Date of Patent: October 22, 1991Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Christian Wegner, Heinz-Joachim Rother
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Patent number: 5047570Abstract: 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: GrantFiled: February 10, 1989Date of Patent: September 10, 1991Assignee: BASF AktiengesellschaftInventor: Ernst Schefczik
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Patent number: 5032598Abstract: 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: GrantFiled: December 8, 1989Date of Patent: July 16, 1991Assignee: Merck & Co., Inc.Inventors: John J. Baldwin, David A. Claremon, Jason M. Elliott, Gerald S. Ponticello, David C. Remy, Harold G. Selnick
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Patent number: 5026853Abstract: 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: GrantFiled: September 20, 1990Date of Patent: June 25, 1991Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Marc G. C. Verdonck
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Patent number: 5011999Abstract: 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: GrantFiled: February 23, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
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Patent number: 4999356Abstract: 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: GrantFiled: December 23, 1988Date of Patent: March 12, 1991Assignee: Hoechst-Roussel Pharmaceuticals, Inc.Inventor: Joseph T. Strupczewski
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Patent number: 4996363Abstract: 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: GrantFiled: December 20, 1988Date of Patent: February 26, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 4990672Abstract: 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: GrantFiled: May 30, 1989Date of Patent: February 5, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Thomas A. Johnson, Ismail O. Abdalmuhdi
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Patent number: 4983735Abstract: 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: GrantFiled: July 20, 1988Date of Patent: January 8, 1991Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 4983736Abstract: 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: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4981965Abstract: 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: GrantFiled: September 9, 1988Date of Patent: January 1, 1991Assignee: Fuji Photo Film Co., Ltd.Inventors: Yoshiharu Yabuki, Jiro Tsukahara, Taku Nakamura
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Patent number: 4977266Abstract: 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: GrantFiled: September 30, 1987Date of Patent: December 11, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 4973692Abstract: 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: GrantFiled: September 30, 1987Date of Patent: November 27, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 4968679Abstract: New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.Type: GrantFiled: May 22, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber, George S. Allen
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Patent number: 4945177Abstract: 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: GrantFiled: December 23, 1986Date of Patent: July 31, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Horst-Juergen Krause, Hans-Theo Leinen, Rudolf Lehmann
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Patent number: 4922024Abstract: 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: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
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Patent number: 4906634Abstract: 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: GrantFiled: March 8, 1988Date of Patent: March 6, 1990Assignee: Schering A.G.Inventors: Stanley S. Greenberg, William C. Lumma, Jr., Klaus Nickisch, Ronald A. Wohl
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Patent number: 4906782Abstract: 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: GrantFiled: August 12, 1987Date of Patent: March 6, 1990Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Yasushi Hara, Sadakatsu Kumoi, Yukihiro Tsutsumi
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Patent number: 4888355Abstract: 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: GrantFiled: December 22, 1987Date of Patent: December 19, 1989Assignee: Roussel UclafInventors: Francois Clemence, Odile Le Martret, Michel Fortin, Francoise Delevallee
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Patent number: 4888425Abstract: 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: GrantFiled: February 7, 1984Date of Patent: December 19, 1989Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: William B. Herdle
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Patent number: 4883797Abstract: 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: GrantFiled: January 7, 1988Date of Patent: November 28, 1989Assignee: Ferrer Internacional, S.A.Inventors: Rafael Foguet, Jose A. Ortiz, Santiago Gubert, Manuel M. Raga, Aurelio Sacristan
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Patent number: 4880808Abstract: 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: GrantFiled: March 9, 1988Date of Patent: November 14, 1989Assignee: Janssen Pharmaceutica N.V.Inventors: Georges H. P. Van Daele, Freddy F. Vlaeminck, Marc G. C. Verdonck
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Patent number: 4877879Abstract: 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: GrantFiled: January 4, 1988Date of Patent: October 31, 1989Assignee: Dow Chemical (Nederland) B.V.Inventor: Michael A. P. Gansow
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Patent number: 4873262Abstract: New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.Type: GrantFiled: December 15, 1987Date of Patent: October 10, 1989Assignee: Bayer AktiengesellschaftInventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber, George S. Allen
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Patent number: 4845297Abstract: 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: GrantFiled: December 30, 1987Date of Patent: July 4, 1989Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4837323Abstract: 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: GrantFiled: May 13, 1987Date of Patent: June 6, 1989Assignee: The Dow Chemical CompanyInventors: Robert G. Martinez, Duane S. Treybig, Terry W. Glass
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Patent number: 4831034Abstract: 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: GrantFiled: August 11, 1987Date of Patent: May 16, 1989Assignee: Rhone-Poulenc SanteInventors: Michel Barreau, Marie-Therese Comte, Jean-Luc Malleron, Gerard Ponsinet
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Patent number: 4816576Abstract: 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: GrantFiled: June 23, 1986Date of Patent: March 28, 1989Assignee: Bayer AkteingesellschaftInventors: Hans-Josef Buysch, Wolfgang Wellner, Hermann Gruber
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Patent number: 4749701Abstract: 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: GrantFiled: December 15, 1986Date of Patent: June 7, 1988Assignee: Mitsubishi Chemical Industries LimitedInventors: Yoshio Hayashi, Tomei Oguri, Masaki Shinoda, Kazuo Takahashi
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Patent number: 4725681Abstract: 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: GrantFiled: August 19, 1985Date of Patent: February 16, 1988Assignee: Ethyl CorporationInventors: Ronald L. Shubkin, Duane C. Hargis
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Patent number: 4709032Abstract: 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: GrantFiled: October 17, 1986Date of Patent: November 24, 1987Assignees: Asahi Kasei Kogyo Kabushiki Kaisha, Hiroyoshi HidakaInventors: Hiroyoshi Hidaka, Takanori Sone
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Patent number: 4698446Abstract: 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: GrantFiled: July 1, 1986Date of Patent: October 6, 1987Assignee: The BF Goodrich CompanyInventors: John T. Lai, Pyong N. Son
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Patent number: 4670592Abstract: 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: GrantFiled: May 7, 1984Date of Patent: June 2, 1987Assignee: Imperial Chemical Industries PLCInventors: Murdoch A. Eakin, Philip N. Edwards, Michael S. Large