Nitrogen Attached Indirectly To The Piperazine Ring By Nonionic Bonding Patents (Class 544/402)
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Patent number: 5861535Abstract: Tertiary aminoaryl compounds, such as N,N'dialkylaminoaryl compounds, are prepared using successive reductive steps without isolation therebetween, at high temperature and pressure. A nitroaryl compound is reduced using a ketone as both solvent and reactant in a reductive environment, and the resulting intermediate is further reacted with an aldehyde in the same reaction mixture without isolation to provide the second substituent on the amino group.Type: GrantFiled: September 23, 1997Date of Patent: January 19, 1999Assignee: Eastman Kodak CompanyInventor: Victor L. Mylroie
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Patent number: 5840725Abstract: Compound represented by the structural formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein: a is 0, 1, 2 or3;b, d and e are independently 0, 1 or 2;R is H, C.sub.1-6 alkyl, --OH or C.sub.2 -C.sub.6 hydroxyalkyl;A is an optionally substituted oxime, hydrazone or olefin;X is a bond, --C(O)--, --O--, --NR.sup.6 --, --S(O)e--, --N(R.sup.6)C(O)--, --C(O)N(R.sup.6)-- --OC(O)NR.sup.6 --, --OC(.dbd.S)NR.sup.6 --, --N(R.sup.6)C(.dbd.S)O--, --C(.dbd.NOR.sup.1)--, --S(O).sub.2 N(R.sup.6)--, --N(R.sup.6)S(O).sub.2 --, --N(R.sup.6)C(O)O-- or --OC(O)--;T is H, phthalimidyl, aryl, heterocycloalkyl, heteroaryl, cycloalkyl or bridged cycloalkyl;Q is --SR.sup.6, --N(R.sup.6)(R.sup.7), --OR.sup.6, phenyl, naphthyl or heteroaryl;R.sup.6a, R.sup.7a, R.sup.8a, R.sup.9a, R.sup.6 and R.sup.7 are H, C.sub.1-6 alkyl, C.sub.2 -C.sub.6 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy-C.sub.1 -C.sub.6 alkyl, phenyl or benzyl; or R.sup.6 and R.sup.7, together with the nitrogen to which they are attached, form a ring;R.sup.Type: GrantFiled: July 25, 1997Date of Patent: November 24, 1998Assignee: Schering CorporationInventors: Gregory A. Reichard, Robert G. Aslanian, Cheryl A. Alaimo, Michael P. Kirkup, Andrew Lupo, Jr., Pietro Mangiaracina, Kevin D. McCormick, John J. Piwinski, Bandarpalle B. Shankar, Neng-Yang Shih, James M. Spitler, Pauline C. Ting, Ashit Ganguly, Nicholas I. Carruthers
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Patent number: 5801179Abstract: The present invention is concerned with compounds having the formula ##STR1## the pharmaceutically acceptable acid addition salts thereof, and the stereochemically isomeric forms thereof, wherein R.sup.1 is hydrogen or C.sub.1--6 alkyl; R.sup.2 is hydrogen or C.sub.1- 6 alkyl; R.sup.3 is C.sub.1-6 alkyl, hydroxy, cyano, halo, C.sub.1-6 alkyloxy, aryloxy, arylmethoxy, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkyl--S--, C.sub.1-6 alkyl(S.dbd.O)--, C.sub.1-6 alkylcarbonyl; R.sup.4 is hydrogen, halo, hydroxy, C.sub.1-6 alkyl, or C.sub.1-6 alkyloxy; or R.sup.3 and R.sup.4 taken together form a bivalent radical; R.sup.5 and R.sup.6 each independently are hydrogen, halo, hydroxy, C.sub.1-6 alkyl, C.sub.1-6 alkyloxy, aryloxy or arylmethoxy; R.sup.7 is hydrogen; Alk.sup.1 is C.sub.2-5 alkanediyl; Alk.sup.2 is C.sub.2-15 alkanediyl; Q is a heterocyclic ring containing at least one nitrogen atom or a radical of formula ##STR2## Pharmaceutical compositions, preparations and use as a medicine are described.Type: GrantFiled: June 2, 1997Date of Patent: September 1, 1998Assignee: Janssen Pharmaceutica, NVInventors: Guy Rosalia Eugene Van Lommen, Marcel Frans Leopold De Bruyn, Piet Tom Bert Paul Wigerinck
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Patent number: 5792769Abstract: Compounds of the formula: ##STR1## wherein R.sup.1 --R.sup.4, R.sup.7 --R.sup.8, R.sup.a, R.sup.b, R.sup.c, Y, Z, n and m are set forth in the specification, as well as hydrates, solvates or pharmaceutically acceptable salts thereof, that inhibit a number of proteolytic enzymes are described. Also described are methods for preparing the compounds of Formula I.Type: GrantFiled: August 15, 1996Date of Patent: August 11, 1998Assignee: 3-Dimensional Pharmaceuticals, Inc.Inventors: Tianbao Lu, Carl R. Illig, Bruce E. Tomczuk, Richard M. Soll, Nalin L. Subasinghe, Roger F. Bone
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Patent number: 5739327Abstract: Bleaching compositions are provided that comprise a nitrile containing compound that has the nitrile bonded to a quaternary nitrogen through a methylene unit (where one or both of the normal hydrogens can be substituted), and two of the quaternary nitrogen bonds are part of a saturated ring. This saturated ring contains from two to eight atoms in addition to the quaternary nitrogen. A source of active oxygen will react with the nitrile for bleaching applications. Particularly preferred nitrile containing compounds are N-alkyl morpholinium acetonitrile salts.Type: GrantFiled: June 7, 1995Date of Patent: April 14, 1998Assignee: The Clorox CompanyInventors: James W. Arbogast, James E. Deline, Lafayette D. Foland, Thomas W. Kaaret, Kevin A. Klotter, Michael J. Petrin, William L. Smith, Alfred G. Zielske
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Patent number: 5739397Abstract: Secondary amines having a hydrocarbon backbone, a functionality of at least 1 and a molecular weight of at least 74 are produced by reacting a hydrocarbon containing a leaving group with a primary amine, primary diamine, primary polyamine or ammonia at a temperature of from about 70.degree. to 250.degree. C.Type: GrantFiled: May 30, 1996Date of Patent: April 14, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5723681Abstract: The present invention relates to novel 3,3-(disubstituted)cyclohexan-1-ol dimers and related compounds, pharmaceutical compositions containing these compounds, and their use in treating allergic and inflammatory diseases and for inhibiting the production of Tumor Necrosis Factor (TNF).Type: GrantFiled: June 23, 1997Date of Patent: March 3, 1998Assignee: SmithKline Beecham CorporationInventors: Siegfried B. Christensen, IV, Joseph M. Karpinski
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Patent number: 5698697Abstract: 2-Cyanopiperazine represented by the following formula (1): ##STR1## or a salt thereof. The 2-cyanopiperazine can be produced by reacting a 2-halogenoacrylonitrile with ethylenediamine or by reacting a 2,3-dihalogenopropionitrile with ethylenediamine.The 2-cyanopiperazine is useful as an intermediate for medicaments, agricultural chemicals, etc., and optically active N-tert-butyl-2-piperazine carboxamide, which is useful as an intermediate in preparation of the HIV protease inhibitor indinavir, can be easily produced using the 2-cyanopiperazine.Type: GrantFiled: July 18, 1996Date of Patent: December 16, 1997Assignee: Mitsubishi Chemical CorporationInventors: Yuki Takuma, Yuzo Kasuga, Takeki Miyazaki, Yuji Mizuho, Ken Okamoto
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Patent number: 5696123Abstract: The invention relates to new compounds of general formula I ##STR1## and the pharmaceutically acceptable salts thereof, wherein A, B, Z, R.sup.1, R.sup.2, R.sup.3 and m are defined as in the specification, processes for preparing them and pharmaceutical compositions containing these compounds. The compounds are valuable neurokinin (tachykinin) antagonists.Type: GrantFiled: June 7, 1995Date of Patent: December 9, 1997Assignee: Boehringer Ingelheim KGInventors: Horst Dollinger, Gerd Schorrenberg, Hans Briem, Birgit Jung, Georg Speck
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Patent number: 5686588Abstract: A stoichiometric acid moiety transfer reaction for the preparation of an acid salt of an amine compound is disclosed. The acid moiety transfer reaction provides amine acid salts of high purity and having crystalline structure of uniform size and shape.Type: GrantFiled: August 16, 1995Date of Patent: November 11, 1997Inventor: Seo Hong Yoo
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Patent number: 5672602Abstract: The present invention relates to substituted piperazine derivatives (herein referred to as compounds or compounds of formula (1)) or stereoisomers, or pharmaceutically acceptable salts thereof and their use as tachykinin receptor antagonists. Such antagonists are useful in the treatment of tachykinin-mediated diseases and conditions disclosed herein including: asthma, cough, and bronchitis.Type: GrantFiled: April 30, 1996Date of Patent: September 30, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Timothy P. Burkholder, Tieu-Binh Le, Elizabeth M. Kudlacz
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Patent number: 5668136Abstract: A benzene, pyridine or pyrimidine derivative having the below shown formula is novel and useful as an anti-arteriosclerotic agent. ##STR1## wherein R.sup.1 stands for a lower alkyl group, an amino group which may be substituted, or the like; R.sup.2 stands for a group represented by the formula: ##STR2## (wherein R.sup.16 stands for an alkyl group having 1 to 6 carbon atoms, or the like) or the like; R.sup.3 stands for a group represented by the formula: --O--(CH.sub.2).sub.m --Y (Y stands for an imidazolyl or piperazinyl group, or the like and m is 1 to 6) or the like; R.sup.5 stands for a hydrogen atom, a lower alkyl group, or the like; A stands for a group represented by the formula: ##STR3## (wherein R.sup.6 stands for a hydrogen atom, a lower alkyl group, or the like), --N.dbd., or the like; and B stands for a group represented by the formula: ##STR4## (wherein R.sup.4 stands for a hydrogen or the like), --N.dbd., or the like.Type: GrantFiled: September 11, 1991Date of Patent: September 16, 1997Assignee: Eisai Co., Ltd.Inventors: Teiji Kimura, Nobuhisa Watanabe, Yasutaka Takase, Kenji Hayashi, Makoto Matsui, Hironori Ikuta, Youji Yamagishi, Kozo Akasaka, Hiroshi Tanaka, Issei Ohtsuka, Takao Saeki, Motoji Kogushi, Tohru Fujimori, Isao Saito
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Patent number: 5620831Abstract: Disclosed are novel cyanoguanidine derivatives which are usable as an epoxy resin curing agent and are represented by the following general formula (1). A thermosetting resin composition and a photocurable and thermosetting resin composition containing the following cyanoguanidine derivatives and other derivatives as the epoxy resin curing agent are also disclosed. ##STR1## wherein R.sup.1 represents a substituent selected from the group consisting of the following substituents (a) through (k).Type: GrantFiled: March 28, 1995Date of Patent: April 15, 1997Assignee: Taiyo Ink Manufacturing Co., Ltd.Inventor: Osamu Kawana
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Patent number: 5599933Abstract: The reaction product of:(a) a compound of the formula: ##STR1## wherein X is a member selected from the group consisting of N, O and S; R.sub.1 and R.sub.2 are independently a straight or branched, saturated or unsaturated non-aromatic hydrocarbon of four to eighteen carbon atoms; m is 1 or 2; and n is 0, 1 or 2; and(b) a compound selected from the group consisting of primary, secondary, tertiary and higher amines, which are liquid at room temperature.The reaction product of the present invention has excellent surfactant properties, and is suitable for use in coloring compositions to improve the fugitivity from skin and clothing. The reaction product is also useful as a cleansing agent.Type: GrantFiled: March 15, 1995Date of Patent: February 4, 1997Assignee: Binney & Smith Inc.Inventor: Richard J. Kaiser
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Patent number: 5580999Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, -N(alkoxycarbonyl)-,-N(acyl)- or --S--or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.Type: GrantFiled: May 12, 1995Date of Patent: December 3, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5571920Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.Type: GrantFiled: January 26, 1996Date of Patent: November 5, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5554641Abstract: The small nonpeptides of the instant invention are tachykinin antagonists. The compounds are highly selective and functional NK.sub.3 antagonists expected to be useful in the treatment of pain, depression, anxiety, panic, schizophrenia, neuralgia, addiction disorders, inflammatory diseases, gastrointestinal disorders, vascular disorders, and neuropathological disorders.Type: GrantFiled: March 20, 1995Date of Patent: September 10, 1996Inventors: David C. Horwell, Martyn C. Pritchard, Jennifer Raphy
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Patent number: 5554793Abstract: 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: December 19, 1994Date of Patent: September 10, 1996Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5516913Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.Type: GrantFiled: May 12, 1995Date of Patent: May 14, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5491263Abstract: 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: GrantFiled: December 21, 1993Date of Patent: February 13, 1996Assignee: The Dow Chemical CompanyInventors: Peter C. Rooney, Michael O. Nutt
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Patent number: 5451678Abstract: Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)-, --N(acyl)- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.Type: GrantFiled: September 29, 1993Date of Patent: September 19, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Kevin E. B. Parkes, Sally Redshaw, Gareth J. Thomas
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Patent number: 5410087Abstract: 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: November 17, 1993Date of Patent: April 25, 1995Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
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Patent number: 5410086Abstract: 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: GrantFiled: June 25, 1991Date of Patent: April 25, 1995Inventor: Lloyd M. Burgess
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Patent number: 5389630Abstract: Diamine compounds of formula (I) or an addition salt thereof are provided: ##STR1## These compounds have an excellent cerebral protective action, are very safe, and exhibit a strong action when orally administered, and therefore, medicines containing such compounds are effective for treating disorders caused by cerebral hemorrhage, cerebral infarction, subarachnoid hemorrhage, transient ischemic attack, cerebrovascular disorders and the like, or preventing progress of such disorders.Type: GrantFiled: January 22, 1993Date of Patent: February 14, 1995Assignee: Kowa Co., Ltd.Inventors: Seiichi Sato, Kiyoshi Kawamura, Yoshio Takahashi, Koichiro Watanabe, Sadahiro Shimizu, Tomio Ohta
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Patent number: 5371088Abstract: 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: GrantFiled: September 14, 1993Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Hans-Joerg Treiber, Hans P. Hofmann, Laszlo Szabo
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Patent number: 5356895Abstract: The present invention relates to compositions and methods for inhibiting nonenzymatic cross-linking (protein aging). Accordingly, a composition is disclosed which comprises; an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. Suitable agents contain an active nitrogen-containing group, such as a hydrazine group. Particular agents comprise aminoguanidine derivatives. the method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.Type: GrantFiled: May 27, 1992Date of Patent: October 18, 1994Assignee: The Rockefeller UniversityInventors: Peter C. Ulrich, Anthony Cerami
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Patent number: 5332816Abstract: The present invention relates to novel piperazine-piperidine compounds of the general formula (I) ##STR1## in which R.sub.1 is e.g. hydrogen or methyl, R.sub.2 is e.g. ethylene, m is zero or 1 and n is e.g. 1, and when n is 1, A is e.g. 2,2-dimethyl-1-propanoyl, n-butoxycarbonyl, n-tetradecyloxycarbonyl or 2,4-bis[N-butyl-(2',2',6',6'-pentamethyl-4'-piperidyl)amino]triazin-6-yl.The said compounds are effective as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials.Type: GrantFiled: July 19, 1990Date of Patent: July 26, 1994Assignee: Ciba-Geigy CorporationInventors: Graziano Vignali, Valerio Borzatta
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Patent number: 5326762Abstract: 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: GrantFiled: May 19, 1992Date of Patent: July 5, 1994Assignee: Schering CorporationInventors: John Clader, Sundeep Dugar, Timothy Kogan, Bradley Tait, Wayne Vaccaro
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Patent number: 5321160Abstract: A process for producing an ethylenamine, which comprises reacting ammonia and/or an ethylenamine with an ethanolamine in the presence of hydrogen to obtain an ethylenamine having an increased number of ethylene chains over the ammonia and/or the ethylenamine used as the starting material, wherein a catalyst comprising Ni, X and M elements wherein X is Re, Ir, Pt or Pd, and when X is Re, Ir or Pb, M is at least one rare earth element selected from the group consisting of scandium, yttrium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium, and when X is Pd, M is at least one member selected from the group consisting of rare earth elements is used for the reaction.Type: GrantFiled: July 29, 1992Date of Patent: June 14, 1994Assignee: Tosoh CorporationInventors: Toshio Hironaka, Noritaka Nagasaki, Yasushi Hara
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Patent number: 5318970Abstract: A isoxazole compound represented by the formula (1): ##STR1## wherein R represents a hydrogen atom or a lower alkoxy group, R.sub.1 is a group represented by the formula (2): ##STR2## (wherein A represents --NH-- or --O--, B represents a methylene group or a carbonyl group, m is 0 or 1, n is an integer of 1 to 12, X represents a hydrogen atom, a hydroxy group or a lower alkoxycarbonyl group, Y represents a phenyl group which can be substituted with one or more halogen atoms, or a hydrogen atom), a group represented by the formula (3): ##STR3## (wherein Z represents a pyrimidinyl group), or a group represented by the formula (4): ##STR4## (wherein R.sub.2 represents a styryl group which can be substituted with one or more hydroxy groups); a pharmaceutically acceptable salt thereof; or a medical use thereof in a method of inhibiting lipoxygenase, inhibiting 5-lipoxygenase or inhibiting cyclooxygenase.Type: GrantFiled: March 17, 1993Date of Patent: June 7, 1994Assignee: Taiho Pharmaceutical Co., Ltd.Inventors: Masahiro Suzuki, Kenji Nozaki, Makoto Kajitani, Mitsugi Yasumoto, Naohiko Ono, Takashi Shindo
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Patent number: 5302720Abstract: Compounds of formula I ##STR1## and their salts in which R.sub.1 is optionally substituted phenyl, R.sub.2 is alkyl, cycloalkyl or optionally substituted amino, or R.sub.2 and R.sub.3 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached form an optionally substituted heterocyclic ring and R.sub.5 is H, halo, alkyl, alkoxy, trifluoromethyl or a group of formula S(O).sub.m R.sub.8 in which m is 0, 1 or 2 and R.sub.8 is alkyl have utility in the treatment of diabetes particularly in the treatment of hyperglycaemia.Type: GrantFiled: June 17, 1992Date of Patent: April 12, 1994Assignee: The Boots CompanyInventor: Balasubramanian Gopalan
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Patent number: 5296633Abstract: The methylated tertiary amines are selectively prepared by reacting a primary or secondary amine, or a nitrile or aminonitrile, including an aminoalcohol, etheramine, a polyamine or fatty polyamine or amidoamine, or amidopolyamine or dinitrile, with hexamethylenetetramine ("HMTA"), under hydrogen pressure at a temperature no greater than about 160.degree. C. and in the presence of a catalytically effective amount of a hydrogenation catalyst, e.g., nickel deposited onto appropriate support substrate therefor.Type: GrantFiled: December 30, 1992Date of Patent: March 22, 1994Inventor: Stephane Fouquay
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Patent number: 5296154Abstract: Improved additives/detergents for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.Type: GrantFiled: April 29, 1993Date of Patent: March 22, 1994Assignee: The Lubrizol CorporationInventor: Thomas F. Steckel
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Patent number: 5288909Abstract: 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: August 19, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5262535Abstract: The reaction product of:(a) a compound of the formula: ##STR1## wherein X is a member selected from the group consisting of N, O and S; R.sub.1 and R.sub.2 are independently a straight or branched, saturated or unsaturated non-aromatic hydrocarbon of four to eighteen carbon atoms; m is 1 or 2; and n is 0, 1 or 2; and(b) a compound selected from the group consisting of primary, secondary, tertiary and higher amines, which are liquid at room temperature.The reaction product of the present invention has excellent surfactant properties, and is suitable for use in coloring compositions to improve the fugitivity from skin and clothing. The reaction product is also useful as a cleansing agent.Type: GrantFiled: February 20, 1992Date of Patent: November 16, 1993Assignee: Binney & Smith Inc.Inventor: Richard J. Kaiser
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Patent number: 5262534Abstract: A process for preparing nonaromatic N,N,N-trisubstituted nitrogen-containing compounds which comprises heating a nonaromatic carboxylated N,N,N-trisubstituted nitrogen-containing compound at an elevated temperature for a period of time sufficient to produce the nonaromatic N,N,N-trisubstituted nitrogen-containing compound.Type: GrantFiled: June 2, 1992Date of Patent: November 16, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5256786Abstract: 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: GrantFiled: March 2, 1992Date of Patent: October 26, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5254689Abstract: 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: GrantFiled: October 7, 1992Date of Patent: October 19, 1993Assignee: American Home Products CorporationInventors: John A. Butera, Jehan F. Bagli, John W. Ellingboe
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Patent number: 5245032Abstract: 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: GrantFiled: September 20, 1990Date of Patent: September 14, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5231230Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 27, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5227528Abstract: A process for decolorizing polyalkylene polyamines, which comprises contacting one or more polyalkylene polyamines having an average molecular weight of greater than about 200 and less than about 1000 with carbon at a temperature greater than or equal to about 100.degree. C. and less than or equal to about 300.degree. C. under conditions effective to reduce the color rating of the one or more polyalkylene polyamines.Type: GrantFiled: April 30, 1992Date of Patent: July 13, 1993Assignee: The Dow Chemical CompanyInventors: Stephen J. Webster, John H. Mitchell
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Patent number: 5225599Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
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Patent number: 5225600Abstract: 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: GrantFiled: August 26, 1992Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5225598Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5223498Abstract: Compounds of formula I ##STR1## and their salts in which n=0 or 1, R.sub.1 and R.sub.2 are each aliphatic or cycloalkyl or NR.sub.1 R.sub.2 is an optionally substituted heterocyclic ring, R.sub.3 is alkyl, cycloalkyl or optionally substituted amino, R.sub.5 is an aliphatic group, R.sub.6 is H, an optionally substituted aliphatic group or a cycloalkyl group, or R.sub.3 and R.sub.5 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R.sub.5 and R.sub.6 together with the nitrogen to which they are attached form a heterocyclic ring optionally substituted by alkyl and R.sub.7 is optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, trifluoromethyl or cyano have utility as hypoglycemic agents.Type: GrantFiled: December 28, 1989Date of Patent: June 29, 1993Assignee: The Boots Company plcInventor: Balasubramanian Gopalan
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Patent number: 5220071Abstract: 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: GrantFiled: March 30, 1990Date of Patent: June 15, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5215989Abstract: 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: GrantFiled: July 15, 1991Date of Patent: June 1, 1993Assignee: 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: 5214215Abstract: 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: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5214213Abstract: 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: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5210306Abstract: 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: GrantFiled: August 8, 1989Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler