The Chalcogen Is Single Bonded To Both Acyclic Carbon And Hydrogen Patents (Class 544/401)
  • Patent number: 5872117
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: February 16, 1999
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5837016
    Abstract: A fuel additive which comprises an amide compound of the formula ##STR1## wherein R.sup.1 is hydrogen or a C.sub.1 -C.sub.30 hydrocarbon group, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 each are selected from the group consisting of hydrogen, a C.sub.1 -C.sub.10 hydrocarbon group and a group of formula (II), provided that at least one of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 group of formula (II) R.sup.6 is a C.sub.2 -C.sub.6 alkylene group, R.sup.7 is a C.sub.1 -C.sub.6 alkylene group, a is an integer of 1-100, b is an integer of 0-100, the sum of a and b being equal to 1-200, c is an integer of 1-3, d is an integer of 0-2, the sum of c and d being equal to 3, and X is selected from the group consisting of hydrogen, a C.sub.1 -C.sub.30 hydrocarbon group, a group of formula (III), and a group of formula (IV), wherein formulas (II), (III) and (IV) are defined in the disclosure.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: November 17, 1998
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Noboru Ishida, Takashi Nakano, Masaki Nagao, Takashi Kaneko
  • Patent number: 5808160
    Abstract: Hydroxyalkyl-substituted aminoalkynes of the general formula I ##STR1## where at least one of the substituents R.sup.1, R.sup.4 or R.sup.5 is hydroxyalkyl are prepared in a reaction with heterogeneous catalysis.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Thomas Preiss, Jochem Henkelmann
  • Patent number: 5807855
    Abstract: Trans isomers of 1-piperazino-1,2-dihydroindene compounds having formula (I), ##STR1## wherein X and Y are hydrogen, halogen, trifluoromethyl, alkyl, alkylthio, trifluoromethylthio, alkoxy, hydroxy, alkylsulfonyl, amino, alkylamino, nitro or cyano; Ar is a phenyl, thienyl or furyl group, each optionally substituted; R.sub.1 is hydrogen, or optionally hydroxy substituted alkyl, alkenyl, cycloalkyl or cycloalkylalkyl; R.sub.2 is alkyl, alkenyl, cycloalkyl, or cycloalkylalkyl; or R.sub.1 and R.sub.2 together form a 5 to 7-membered heterocyclic ring fused with the piperazine ring, which ring may be substituted with hydroxy; R.sub.3 is hydrogen, alkyl, alkenyl, cycloalkyl or cycloalkylalkyl; or R.sub.2 and R.sub.3 together form a 3 to 7-membered carbocyclic ring which is spiro-fused to the piperazine ring; and R.sub.4 is hydrogen or alkyl. The compounds of the invention have potent antagonist action on dopamine D.sub.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: September 15, 1998
    Assignee: H. Lundbeck A/S
    Inventors: Klaus B.o slashed.ges.o slashed., Peter Bregnedal
  • Patent number: 5801175
    Abstract: Novel compounds of Formula ##STR1## are disclosed. Also disclosed is a method of inhibiting Ras function and therefore inhibiting the abnormal growth of cells. The method comprises administering a compound of the above formula to a biological system. In particular, the method inhibits the abnormal growth of cells in a mammal such as a human being.
    Type: Grant
    Filed: September 13, 1996
    Date of Patent: September 1, 1998
    Assignees: Schering Corporation, Pharmacopeia, Inc.
    Inventors: Adriano Afonso, John J. Baldwin, Ronald J. Doll, Ge Li, Alan K. Mallams, F. George Njoroge, Dinanath F. Rane, John C. Reader, Randall R. Rossman
  • Patent number: 5773617
    Abstract: The present invention relates to a reagent and to a process which are useful, when carrying out an organic synthesis, for cleaving an allylic group from a function which is protected with the latter.This reagent is defined in that it contains:a) a solvent system;b) a catalyst containing at least one element from column VIII of the Periodic Table of the Elements, the said element from column VIII of the Periodic Table being coordinated with at least one coordination agent which is soluble in the said solvent system;c) a compound which is at least partially soluble in the said solvent system and which contains at least one nucleophilic function.Application to organic synthesis.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: June 30, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Marie Bernard, Errol Blart, Jean-Pierre Genet, Sandrine Lemaire-Audoire, Monique Savignac
  • Patent number: 5641783
    Abstract: Disclosed are compounds having a straight or branched aliphatic hydrocarbon structure of formula I: ##STR1## In formula I, n is an integer from one to four and m is an integer from four to twenty. Independently, R.sub.1 and R.sub.2 are hydrogen, a straight or branched chain alkyl, alkenyl or alkynyl of up to twenty carbon atoms in length or --(CH.sub.2).sub.w R.sub.5. If R.sub.1 or R.sub.2 is --(CH.sub.2).sub.w R.sub.5, w may be an integer from one to twenty and R.sub.5 may be an hydroxyl, halo, C.sub.1-8 alkoxyl group or a substituted or unsubstituted carbocycle or heterocycle. Alternatively, R.sub.1 and R.sub.2 may jointly form a substituted or unsubstituted, saturated or unsaturated heterocycle having from four to eight carbon atoms, N being a hetero atom of the resulting heterocycle. R.sub.3 may be either hydrogen or C.sub.1-3. In the compounds, a total sum of carbon atoms comprising R.sub.1 or R.sub.2, (CH.sub.2).sub.n and (CH.sub.2).sub.m does not exceed forty. R.sub.
    Type: Grant
    Filed: September 8, 1994
    Date of Patent: June 24, 1997
    Assignee: Cell Therapeutics, Inc.
    Inventors: J. Peter Klein, Gail E. Underiner, Anil M. Kumar
  • Patent number: 5604229
    Abstract: 2-Amino-1,3-propanediol compounds of the formula (I) ##STR1## wherein R is an optionally substituted straight- or branched carbon chain, an optionally substituted aryl, an optionally substituted cycloalkyl or the like, and R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and each is a hydrogen, an alkyl, an aralkyl, an acyl or an alkoxycarbonyl, pharmaceutically acceptable salts thereof and immunosuppressants comprising these compounds as active ingredients.The 2-amino-1,3-propanediol compounds of the present invention show immunosuppressive action and are useful for suppressing rejection in organ or bone marrow tranplantation, prevention and treatment of autoimmune diseases or as reagents for use in medicinal and pharmaceutical fields.
    Type: Grant
    Filed: June 17, 1994
    Date of Patent: February 18, 1997
    Assignees: Yoshitomi Pharmaceutical Industries, Ltd., Taito Co., Ltd.
    Inventors: Tetsuro Fujita, Shigeo Sasaki, Masahiko Yoneta, Tadashi Mishina, Kunitomo Adachi, Kenji Chiba
  • Patent number: 5563271
    Abstract: Preparation of N-(2-sulfatoethyl)piperazine sulfate by reacting N-(2-hydroxyethyl)piperazine in a mixture of high- or relatively high-percentage sulfuric acid and oleum or chlorosulfonic acid at temperatures of about 80.degree. C. to about 250.degree. C., introducing the sulfation mixture formed into a water-miscible aliphatic alcohol and isolating the N-(2-sulfatoethyl)piperazine sulfate formed.
    Type: Grant
    Filed: March 15, 1995
    Date of Patent: October 8, 1996
    Assignee: Hoechst AG.
    Inventors: Michael Meier, Heinz-Georg Kautz, Andreas Schrell
  • Patent number: 5554793
    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: December 19, 1994
    Date of Patent: September 10, 1996
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5492913
    Abstract: The compounds are N-(unsubstituted or substituted) N'-benzylpiperazine compounds and pharmaceutically tolerable salts thereof, useful for treating neuronal disorders resulting from the dysfunctioning of oxidative metabolism.A compound disclosed is: N-ethyl N'-(2-hydroxy-3,4- dimethoxybenzyl)-piperazine and its dihydrochloride.
    Type: Grant
    Filed: March 23, 1994
    Date of Patent: February 20, 1996
    Assignee: Adir et Compagnie
    Inventors: Michel Wierzbicki, Jean Lepagnol, Jean-Paul Tillement, Bernard Testa, Yves Rolland
  • Patent number: 5491263
    Abstract: A process is disclosed for producing a substituted ethylenediamine, the process comprising reacting an oxazolidinone with a secondary amine or an alkanolamine. The process includes, in one aspect, reacting precursors of the oxazolidinone in situ.
    Type: Grant
    Filed: December 21, 1993
    Date of Patent: February 13, 1996
    Assignee: The Dow Chemical Company
    Inventors: Peter C. Rooney, Michael O. Nutt
  • Patent number: 5476969
    Abstract: The invention relates to highly reactive polyoxyalkylene-polyols prepared by oxyalkylation of an initiator molecule containing, in bonded form, at least 2 reactive hydrogen atoms and at least one tertiary amino group bonded via a spacer bridge, which preferably comprises an alkylene radical having at least 3 carbon atoms, by means of at least one alkylene oxide, preferably ethylene oxide and/or 1,2-propylene oxide, to a process for the preparation of these polyoxyalkylene-polyols, and to their use for the production of compact or cellular, preferably flexible polyisocyanate polyaddition products.
    Type: Grant
    Filed: September 28, 1992
    Date of Patent: December 19, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Hinz, Stefan Adams, Ulrich Koehler, Christian Maletzko, Klaus Vorspohl, Ruth Zschiesche
  • Patent number: 5472984
    Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.
    Type: Grant
    Filed: December 29, 1993
    Date of Patent: December 5, 1995
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5464941
    Abstract: The present invention provides novel substituted biphenyl pyrazines or pyrazine derivatives ("BPD") which are functional and have useful application as a monomer for a variety of high performance polymers such as polyester, polyarylate, polycarbonate, polyetherketones, epoxides, polyimides, polyamides, and polyamides-imides; and as pigments for coating compositions such as paints.
    Type: Grant
    Filed: October 19, 1994
    Date of Patent: November 7, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, George Kvakovszky, Olan S. Fruchey, Hans J. Metz
  • Patent number: 5455352
    Abstract: Preparation of N-(2-hydroxyethyl)-piperazine by reacting triethanolamine with ammonia in the presence of hydrogen at from 100.degree. to 500.degree. C. and from 10 to 500 bar over a heterogeneous catalyst in which the catalytically active material contains from 20 to 85% by weight of ZrO.sub.2 or Al.sub.2 O.sub.3 or mixtures thereof, from 1 to 30% by weight of at least one copper oxide, calculated as CuO, and from 1 to 60% by weight of at least one oxide of cobalt, nickel or molybdenum, calculated as CoO, NiO and MoO.sub.3, respectively.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: October 3, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Huellmann, Rainer Becker, Emil Scharf
  • Patent number: 5409931
    Abstract: 1,3-Substituted cycloalkenes and cycloalkanes are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and antihypertensive agents as well as for treating hyperprolactinaemia-related conditions and central nervous system disorders.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: April 25, 1995
    Assignee: Warner-Lambert Company
    Inventors: Bradley W. Caprathe, Dennis M. Downing, Juan C. Jaen, Stephen J. Johnson, William J. Smith, III, Lawrence D. Wise, Jonathan Wright, David J. Wustrow
  • Patent number: 5410087
    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: November 17, 1993
    Date of Patent: April 25, 1995
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
  • Patent number: 5410086
    Abstract: This invention relates to a method for controlling the weight ratio of diethylenetriamine to piperazine in a process in which ethylenediamine, or a mixture of ethylenediamine and monoethanolamine, and hydrogen are maintained in the presence of a hydrogenation catalyst, which method comprises adjusting the hydrogen concentration in the liquid phase in an amount sufficient to effectuate control of the weight ratio of diethylenetriamine to piperazine in said process.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: April 25, 1995
    Inventor: Lloyd M. Burgess
  • Patent number: 5371088
    Abstract: Compounds of the formula ##STR1## where Ar, R.sup.1, R.sup.2, P and Q have the meanings indicated in the description, and the preparation thereof are described. The compounds have antihypoxic and antiischemic action and are suitable for treating acute and chronic degenerative processes of the CNS and other organs.
    Type: Grant
    Filed: September 14, 1993
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Joerg Treiber, Hans P. Hofmann, Laszlo Szabo
  • Patent number: 5367050
    Abstract: A polyether polyol produced by using an N-amino-ethylpiperazine-ethylene oxide aduct as an initiator and addition-polymerizing an alkylene oxide thereto and having a molecular weight of about 2000 to 7000; a process for producing a flexible urethane foam starting with the above polyether polyol; a process suited for the production of a hot-cure urethane foam which comprises using the above polyether polyol with a hydroxyl value of 40 to 80 mg KOH/g and, as a blowing agent, 4.6 to 6.0 weight parts of water based on 100 weight parts of the polyol; and a process suited for the production of a cold-cure urethane foam which comprises using the above polyether polyol with a hydroxyl value of 23 to 50 mg KOH/g and, as a blowing agent, 2.5 to 5.0 weight parts of water on the same basis.
    Type: Grant
    Filed: February 16, 1994
    Date of Patent: November 22, 1994
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Yoshihiko Tairaka, Mitsuhiro Nishimura, Katsuhisa Kodama
  • Patent number: 5352677
    Abstract: Cinnamamide derivatives and the salts thereof are provided. An antihyperlipidemic composition is also provided. The composition comprises an active ingredient which is at least one selected from the group consisting of the above-mentioned cinnamamide derivative and the pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: July 15, 1992
    Date of Patent: October 4, 1994
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshihide Fuse, Kenji Fujii, Keiji Kameyama, Taizo Kawabe, Toshiaki Miwa, Ikuo Katsumi
  • Patent number: 5326873
    Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: July 5, 1994
    Assignee: Eastman Kodak Company
    Inventors: Stephen A. Godleski, Yann Hung
  • Patent number: 5326762
    Abstract: Amides of the formula ##STR1## wherein R.sub.1 and R.sub.2 are independently heteroaryl, X-substituted heteroaryl, X-substituted phenyl, N-substituted triazinyl or N-substituted imidazolyl;and in addition, one of R.sub.1 and R.sub.2 can be as defined above and the other can be phenyl;R.sub.3 is an alkyl chain of 2 to 25 carbon atoms, saturated or unsaturated; an alkyl chain as defined substituted by one or more substituents selected from the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl; an alkyl chain as defined interrupted by one or more groups independently selected from the group consisting of --O--, --S--, --SO--, --SO.sub.2 --, --NH--, --N(lower alkyl)--, --C(O)--, phenylene, X-substituted phenylene, heteroarylene and X-substituted heteroarylene; or an interrupted alkyl chain as defined substituted by one or more substituents selected form the group consisting of phenyl, X-substituted phenyl, heteroaryl and X-substituted heteroaryl;R.sub.
    Type: Grant
    Filed: May 19, 1992
    Date of Patent: July 5, 1994
    Assignee: Schering Corporation
    Inventors: John Clader, Sundeep Dugar, Timothy Kogan, Bradley Tait, Wayne Vaccaro
  • Patent number: 5292910
    Abstract: A process for the catalyzed ethoxylation or propoxylation of compounds selected from the group consisting of organic compounds containing active H atoms, esters of fatty acids containing 2 to 22 carbon atoms with monoalkanols containing 1-22 carbon atoms with polyols containing 2 to 12 carbon atoms and 2 to 6 hydroxyl groups, wherein the improvement comprises the use as catalyst for the ethoxylation or propoxylation of hydrophobicized hydrotalcites corresponding to the general formula I:Mg.sub.x Al(OH).sub.y (CO.sub.3).sub.m (A).sub.n.zH.sub.2 O (I),in which A is selected from the group consisting of (i) a dianion of an aliphatic dicarboxylic acid containing 4 to 44 carbon atoms and (ii) two anions of aliphatic monocarboxylic acids containing 2 to 34 carbon atoms; 1<x<5; y.ltoreq.2x+2; {y+2(m+n)}=2x+3; m+n.ltoreq.0.5; m.gtoreq.0; and 0<z<10.
    Type: Grant
    Filed: December 2, 1992
    Date of Patent: March 8, 1994
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Hans-Christian Raths, Wolfgang Breuer, Klaus Friedrich, Klaus Herrmann
  • Patent number: 5288909
    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: August 19, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5284850
    Abstract: Novel terpene amino alcohols having an antiallergic activity or an activity of improving cerebral function are provided. Also provided are medicinal uses of the alcohols.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: February 8, 1994
    Assignee: Kuraray Co., Ltd.
    Inventors: Koichi Kanehira, Katsushi Eziri, Manzo Shiono, Yoshiji Fujita, Johji Yamahara
  • Patent number: 5283246
    Abstract: The compounds are substituted trimetazidine useful for the treatment of ischaemic pathologies and peripheral vascular pathology.A compound disclosed is 4-(2,3,4-trimethoxybenzyl)-1-[3-(4-hydroxy-2,3,5-trimethylphenoxy)propyl]p iperazine.
    Type: Grant
    Filed: September 17, 1992
    Date of Patent: February 1, 1994
    Assignee: Adir et Compagnie
    Inventors: Gilbert Regnier, Jean-Paul Vilaine, Nicole Villeneuve, Jean-Pierre Bidouard, Jean-Pierre Iliou, Albert Lenaers
  • Patent number: 5281595
    Abstract: The invention relates to compounds having anti-ischaemic activity, memory enhancing activity and anti-convulsive activity of the formulae 1A and 1B ##STR1## wherein R.sub.1 +R.sub.2 together form an alkylene group having 1-3 C-atoms which may be substituted with one or more alkyl group(s) having 1-3 C-atoms and the remaining R and Z variables are defined as disclosed herein, or a pharmacologically acceptable salt thereof.
    Type: Grant
    Filed: March 17, 1992
    Date of Patent: January 25, 1994
    Assignee: Duphar International Research B.V.
    Inventors: Josephus H. M. Lange, Gerrit P. Toorop, Ineke v. Wijngaarden, Jacobus A. J. den Hartog
  • Patent number: 5256786
    Abstract: A process of reforming cyclic alkyleneamines to amine-extended cyclic alkyleneamines involving contacting a cyclic alkyleneamine or mixture of cyclic alkyleneamines in the liquid phase with a catalyst under reaction conditions. The catalyst is selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB and VB, and (d) specified tungsten oxides. For example, piperazine or a mixture of piperazine and aminoethylpiperazine is contacted with magnesium silicate to yield a mixture of amine-extended piperazines, including 1,2-bis(piperazinyl)-ethane and N,N'-bis(2-piperazinylethyl)piperazine.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: October 26, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5254689
    Abstract: Compounds of the formula: ##STR1## in which R.sup.1 is alkylsulfonamido of 1 to 6 carbon atoms, arylsulfonamido of 6 to 10 carbon atoms, --NO.sub.2, --CN, 1-imidazolyl or 1,2,4-triazol-1-yl;Y is ##STR2## --CH.sub.2 --, --O--, --S--, or --SO.sub.2 --; X is --CH.dbd. or --N.dbd.;R.sup.2 is hydrogen when n is 0, otherwise it is hydrogen or --OH;n is one of the integers 0, 1, 2, 3, 4, 5 or 6;A is ##STR3## where R.sup.3 is alkylsulfonamido of 1 to 6 carbon atoms, arylsulfonamido of 6 to 10 carbon atoms, --NO.sub.2, --CN, 1-imidazolyl or 1,2,4-triazol-1-yl; or ##STR4## where R.sup.4 is hydrogen or alkyl of 1 to 6 carbon atoms; with the provisos that:a) X is --CH.dbd. when Y is ##STR5## --O-- or --S-- and when Y is ##STR6## and R.sup.2 is --OH; b) X is --N.dbd. when A is ##STR7## and c) A is ##STR8## when Y is --S-- or --SO.sub.2 -- and X is --CH.dbd., and their pharmaceutically acceptable salts are Class III antiarrhythmic agents.
    Type: Grant
    Filed: October 7, 1992
    Date of Patent: October 19, 1993
    Assignee: American Home Products Corporation
    Inventors: John A. Butera, Jehan F. Bagli, John W. Ellingboe
  • Patent number: 5247087
    Abstract: Dithiocarbamic salts made from the reaction products of certain polyamines and epoxides have been found to be useful to clarify water, particularly the oil-in-water emulsions which accompany crude oil production. The water clarification may be accomplished by demulsification or flocculation. The polyamine reaction products themselves are novel and may have the structure ##STR1## where R" is selected from the group consisting of the structure --R--NH.sub.2 and ##STR2## where R is selected from the group consisting of straight, branched or cyclic alkylene moieties; arylene moieties; substituted straight, branched or cyclic alkylene moieties; substituted arylene moieties or mixtures thereof; and where R' is--(CH.sub.2).sub.m --O--R--O--(CH.sub.2).sub.m --where n and m independently range from 1 to 5 and q is 0 or 1. The dithiocarbamic salts made from these polyamines also find use as corrosion inhibitors.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: September 21, 1993
    Assignee: Baker Hughes Incorporated
    Inventor: Gordon T. Rivers
  • Patent number: 5245032
    Abstract: A process for preparing N,N,N-trisubstituted nitrogen-containing compounds which comprises contacting a carboxylated N,N,N-trisubstituted nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the N,N,N-trisubstituted nitrogen-containing compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: September 14, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5239105
    Abstract: Diphenylcarbonate is produced by contacting phenol with phosgene or phenylchloroformate or mixture thereof in the presence of one or more heterogeneous catalysts. The catalysts include Group VB metal oxides: silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals: tungsten oxides: and clays. The more preferred catalysts are silicates of yttrium, titanium, or zirconium.
    Type: Grant
    Filed: January 30, 1992
    Date of Patent: August 24, 1993
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, Robert G. Bowman
  • Patent number: 5234934
    Abstract: The invention relates to novel racemic or optically active aminopropanol derivatives of formula I ##STR1## wherein R and R.sup.1 are independently hydrogen atom, halogen atom, lower alkoxy, or together represent a methylene dioxy group,R.sup.2 and R.sup.3 together represent a chemical bond or independently stand for a hydrogen atom,R.sup.4 and R.sup.5 are independently hydrogen atom, C.sub.3-7 cycloalkyl group or straight or branched, saturated or unsaturated C.sub.1-12 alkyl group optionally substituted by one or more dialkyl-aminoalkyl, dimethoxyphenyl or phenyl groups, orR.sup.4 and R.sup.5 together with the adjacent nitrogen atom form a 4 to 7 membered ring optionally comprising an oxygen, sulfur or a further nitrogen atom, which ring is optionally substituted by a phenyl, benzyl or C.sub.1-3 alkyl group and the said substituents may carry a hydroxyl group, one or two methoxy groups, halogen atoms or trifluoromethyl groups, orR.sup.4 and R.sup.
    Type: Grant
    Filed: April 30, 1992
    Date of Patent: August 10, 1993
    Assignee: Egis Gyogyszergyar
    Inventors: Zoltan Budai, Klara Reiter nee Esses, Eniko Sziri nee Kiszelly, Gizella Zsila, Gabor Gigler, Lujza Petocz, Maria Szecsey nee Hegedus, Marton Fekete, Valeria Hoffmann, Laszlo Kapolnai
  • Patent number: 5231230
    Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a metallic phosphate having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during the process, a metallic polyphosphate having a condensed structure, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 27, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
  • Patent number: 5225600
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a Group VIB metal-containing condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 26, 1992
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 5225599
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear triethylenetetramine (L-TETA) 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 L-TETA and AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
  • Patent number: 5225598
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear pentaethylenehexamine (L-PEHA) and hydroxyethyldiethylenetriamine (HEDETA) 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 L-PEHA and HEDETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
  • Patent number: 5220071
    Abstract: This invention relates to a process for making amines having a high yield weight percent of pentaethylenehexamine (PEHA) and hydroxyethyltriethylenetetramine (HETETA) 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 PEHA and HETETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: June 15, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
  • Patent number: 5215989
    Abstract: Compounds of structural formula: ##STR1## wherein Ar is an aromatic ring, B is a cyclic moiety fused to Ar of 5-7 members, X and Y are bridging groups, Q is a nitrogen containing heterocycle, R.sup.2 and R.sup.3 are H, substituted or unsubtituted C.sub.1-3 alkyl, C.sub.1-3 alkoxy, N(R).sub.2, halogen, CF.sub.3 or R.sup.5 and R.sup.1 is H or an aryl group.
    Type: Grant
    Filed: July 15, 1991
    Date of Patent: June 1, 1993
    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: 5214142
    Abstract: A process for preparing aminoethers, particularly bis[2-(N,N-dialkylamino)alkyl]ethers, which comprises contacting a carboxylated aminoether with a metal oxide catalyst under conditions effective to produce the aminoether. Many of these aminoethers are useful as catalysts in the production of polyurethanes, especially cellular polyurethanes.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: May 25, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5214213
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear tetraethylenepentamine (L-TEPA) and hydroxyethyldiethylenetriamine (HEDETA) 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 L-TEPA and HEDETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: May 25, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
  • Patent number: 5214215
    Abstract: This invention relates to a process for making amines having a high yield weight percent of 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 AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: May 25, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
  • Patent number: 5210307
    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: January 31, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5210306
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a condensation catalyst and a condensation catalyst promoter, wherein said condensation catalyst promoter is present in an amount sufficient to promote the condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
  • 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: 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: 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: 5171753
    Abstract: Derivatives of 2-amino-1-phenylethanol were prepared from substituted amines and benzoin, stilbene oxide or styrene oxide to give compounds of Formula: ##STR1## where R is H or (un)substituted phenyl and C is a linking group or terminal group. The compounds of this invention can inhibit ulceration in in-vivo studies in rats.
    Type: Grant
    Filed: May 15, 1991
    Date of Patent: December 15, 1992
    Assignee: A. H. Robins Company, Incorporated
    Inventors: Harry R. Munson, Jr., Robert F. Boswell