Nitroxides, Oxyamines Or Hydroxylamines (i.e., Hnh-o Or Hnh-oh, Wherein Substitution May Be Made For Hydrogen Only, Including O-ether And O-ester Derivatives) Patents (Class 564/300)
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Patent number: 6512136Abstract: New compounds of formula I are described The compounds have potentially valuable pharmaceutical properties in the treatment of some central and peripheral nervous system disorders, where a reduction in the O-methylation of catecholamines may be of therapeutical benefit, such as Parkinson's disease and parkinsonian disorders, gastrointestinal disturbances, edema formation states and hypertension.Type: GrantFiled: December 17, 1999Date of Patent: January 28, 2003Assignee: Portela & C.A., S.A.Inventors: Jan Benes, Patricio Manuel Viera Araujo Soares Da Silva, David Alexander Learmonth
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Patent number: 6512143Abstract: Novel salts of N-tert-butylhydroxylamine with lower carboxylic acids are disclosed, together with processes for their preparation. The salts possess advantageous properties that render them useful in synthesis.Type: GrantFiled: September 2, 1999Date of Patent: January 28, 2003Assignee: AstraZeneca ABInventor: Jörgen Blixt
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Patent number: 6495720Abstract: The invention relates to a process for preparing alkoxyamines. This process consists in mixing, in an organic solvent, a metal salt, a ligand for the metal, a halocarbon compound ZX and a nitroxide, in keeping the reaction medium stirring at a temperature of between 20° C. and 90° C. until the nitroxide has disappeared, in recovering the organic phase, in washing it with water and then in isolating the alkoxyamine by evaporating the organic solvent under reduced pressure.Type: GrantFiled: February 23, 2001Date of Patent: December 17, 2002Assignee: AtofinaInventors: Jean-Luc Couturier, Olivier Guerret, Thierry Senninger
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Patent number: 6492405Abstract: The present invention provides a compound containing at least one sulfhydryl group and at least one NO donor group, wherein said compound is a) a compound containing one or more sulfhydryl groups linked to at least one aromatic ring or a heteroaromatic ring with a nitrogen in the ring structure, which ring is substituted by one or more substituents bearing a terminal —ONO2 group; b) a 5-membered ring heterocyclic compound containing a sulfur atom and a nitrogen atom, which ring is substituted by one or more substituents bearing a terminal —ONO2 group; c) a 5-membered ring compound containing two conjugate S-atoms, which ring is linked to one or more substituents bearing a terminal —ONO2 group; or d) a compound containing an acyclic —S—S group, linked to at least one aromatic ring or a heteroaromatic ring with a nitrogen in the ring structure, which ring is substituted by one or more substituents bearing a terminal —ONO2 group.Type: GrantFiled: January 9, 2002Date of Patent: December 10, 2002Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventor: Abdullah Haj-Yehia
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Patent number: 6489365Abstract: Compounds of the formula which is explained more fully in the specification, may be prepared by conventional methods and used therapeutically in conventional galenic preparations.Type: GrantFiled: January 18, 2000Date of Patent: December 3, 2002Assignee: Boehringer Ingelheim KGInventors: Ralf Anderskewitz, Kurt Schromm, Ernst-Otto Renth, Frank Himmelsbach, Franz Birke, Armin Fugner
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Patent number: 6479552Abstract: The invention relates to substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted diamines.Type: GrantFiled: November 14, 2001Date of Patent: November 12, 2002Assignee: G.D. Searle & Co.Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
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Patent number: 6479697Abstract: A process for the preparation of &agr;-(2,4-disulfophenyl)-N-tert-butylnitrone diacids and pharmaceutically acceptable salts thereof by the reaction of the corresponding disulfophenyl aldehyde with N-tert-butylhydroxylammonium acetate is disclosed.Type: GrantFiled: April 5, 2001Date of Patent: November 12, 2002Assignee: AstraZeneca ABInventors: Henry Kruk, John McGinley, Sergei Pouhov, John Vajda, Jörgen Blixt
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Patent number: 6451823Abstract: The invention relates to use of substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N-phenoxy-N-phenyl aminoalcohols.Type: GrantFiled: November 14, 2001Date of Patent: September 17, 2002Assignee: G.D. Searle & Co.Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
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Patent number: 6441032Abstract: Disclosed are novel &agr;-aryl-N-alkylnitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for preventing and/or treating neurodegenerative, autoimmune and inflammatory conditions in mammals and as analytical reagents for detecting free radicals.Type: GrantFiled: August 9, 2000Date of Patent: August 27, 2002Assignee: Centaur Pharmaceuticals, Inc.Inventors: Judith A. Kelleher, Kirk R. Maples, Alina Dykman, Yong-Kang Zhang, Allan L. Wilcox, Julian Levell
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Patent number: 6420573Abstract: This invention provides processes for the preparation of a compound of Formula I: Y—C(═O)—C(R1)(R2)—CH2—S(O)nR3 wherein: Y is hydroxy or XONX, where each X is independently hydrogen, lower alkyl or lower acyl; R1 is hydrogen or lower alkyl; R2 is hydrogen, lower alkyl, aryl, aralkyl, cycloalkyl, cycloalkylalkyl, or R1 and R2 together with the carbon atom to which they are attached form a cycloalkyl or heterocyclo group; R3 is aryl; and n is 0, 1 or 2. The invention also provides novel aryl haloalkyl sulfide intermediates useful for the preparation of compounds of Formula I and novel methods of preparing aryl alkyl sulfides.Type: GrantFiled: November 9, 2001Date of Patent: July 16, 2002Assignee: Syntex (U.S.A.) LLPInventors: Jeffrey Allen Campbell, Lawrence Emerson Fisher, Charles Alois Dvorak, Paul Leo McGrane
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Publication number: 20020082453Abstract: This invention relates to a process for preparing N-substituted hydroxylamines from N-substituted aryl- or heteroaryloxaziridines by acid hydrolysis and isolation of the N-substituted hydroxylamines in the form of their salts.Type: ApplicationFiled: December 7, 2001Publication date: June 27, 2002Inventors: Michael Dockner, Wolfgang Eymann, Bernd-Michael Konig, Helmut Holzem
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Publication number: 20020061989Abstract: This invention concerns the preparation of polymers of low polydispersity and/or controlled molecular weight and architecture employing living free radical polymerization initiated by an alkoxyamine initiator or nitroxide plus, optionally, a free radical initiator; the polymer produced thereby; selected nitroxide and alkoxyamine initiators; and a process for making the initiators; the polymeric products being useful in protective coatings.Type: ApplicationFiled: May 9, 2001Publication date: May 23, 2002Inventors: Albert G. Anderson, Alexei Gridnev, Graeme Moad, Ezio Rizzardo, San Hoa Thang
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Publication number: 20020058772Abstract: The present invention concerns the preparation of polymers of low polydispersity and/or controlled molecular weight and architecture employing living free radical polymerization initiated by an alkoxyamine initiator or nitroxide plus, optionally, a free radical initiator, the polymer produced thereby; selected nitroxide and alkoxyamine initiators; and a process for making the initiators; the polymeric products being useful in protective coatings.Type: ApplicationFiled: May 9, 2001Publication date: May 16, 2002Inventors: Albert G. Anderson, Alexei Gridnev
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Patent number: 6362183Abstract: An aromatic sulfonyl alpha-hydroxy hydroxamic acid compound that, inter alia, inhibits matrix metalloprotease activity is disclosed, as is a treatment process that comprises administering a contemplated aromatic sulfonyl alpha-hydroxy hydroxamic acid compound in an MMP enzyme-inhibiting effective amount to a host having a condition associated with pathological matrix metalloprotease activity.Type: GrantFiled: June 4, 1999Date of Patent: March 26, 2002Assignee: G. D. Searle & CompanyInventors: John N. Freskos, Terri L. Boehm, Brent V. Mischke, Robert M. Heintz, Joseph J. McDonald, Gary A. DeCrescenzo, Susan C. Howard
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Patent number: 6359182Abstract: A C-nitroso compound having a molecular weight ranging from about 225 to about 1,000 (from about 225 to about 600 for oral administration) on a monomeric basis wherein a nitroso group is attached to a tertiary carbon, which is obtained by nitrosylation of a carbon acid having a pKa less than about 25, is useful as an NO donor. When the compound is obtained from a carbon acid with a pKa less than about 10, it provides vascular relaxing effect when used at micromolar concentrations and this activity is potentiated by glutathione to be obtained at nanomolar concentrations. When the compound is obtained from a carbon acid with a pKa ranging from about 15 to about 20, vascular relaxing effect is obtained at nanomolar concentrations without glutathione. The compound is preferably water-soluble and preferably contains a carbon alpha to the nitrosylated carbon which is part of a ketone group.Type: GrantFiled: October 26, 2000Date of Patent: March 19, 2002Assignee: Duke UniversityInventors: Jonathan S. Stamler, Eric J. Toone
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Publication number: 20020007585Abstract: Sterically hindered N-substituted aryloxyamines are prepared by the transition-metal-catalyzed decomposition of diazonium salts in the presence of a sterically hindered nitroxyl radical. These compounds are useful as thermal and light stabilizers for a variety of organic substrates.Type: ApplicationFiled: April 2, 2001Publication date: January 24, 2002Inventors: Stephen D. Pastor, Sai Ping Shum
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Patent number: 6291702Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be colorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: February 8, 2000Date of Patent: September 18, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Publication number: 20010018452Abstract: Compounds of formula 1 1Type: ApplicationFiled: December 13, 2000Publication date: August 30, 2001Inventors: Henry Szczepanski, Martin Zeller, Hugo Ziegler
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Patent number: 6265614Abstract: Intermediates having the formula wherein BI is —CH2OH or —CH2ORP, and RP is an alcohol protecting group; a is 1, 2, or 3; TI is —OH or QI is phenyl, naphthyl ohr heteroaryl having 1-3 substituents; Ra and Rc are the same, and are H, or are selected from alkyl, cycloalkyl and aryl groups, the groups being optionally substituted with one or more substituents selected from alkyl cycloalkyl, aryl, or —OH; or Ra and Rc together with the C—N—C chain to which they are bound, form a 5-7 membered ring; Rb and Rd are the same, and are H, or are selected from alkyl, cycloalkyl and aryl groups, the groups being optionally substituted with one or more substituents selected from alkyl, cycloalkyl, aryl, or —OH; and D is a directing group capable of directing lithiation alpha to a nitrogen atom of a nitrogen compound having D as a substituent bound to the nitrogen atom when the nitrogen compound is reacted with s-butyl lithium, are disclosedType: GrantFiled: October 13, 2000Date of Patent: July 24, 2001Assignee: Schering CorporationInventors: Anantha R. Sudhakar, Suhan Tang
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Patent number: 6258775Abstract: The invention relates to novel biaromatic compounds having general formula I and their use in pharmaceutical compositions for use in human and veterinary medicine, in particular for treating dermatological, rheumatic, respiratory, cardiovascular, and ophthalmological disorders, and for use in cosmetic compositions.Type: GrantFiled: November 17, 1997Date of Patent: July 10, 2001Assignee: Centre International de Recherches Dermatologiques GaldermaInventors: Jean-Michel Bernardon, Philippe Diaz
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Patent number: 6258983Abstract: The present invention comprises a process of producing HAN by slowly adding nitric acid to an alcoholic solution of hydroxylamine. This forms a precipitate of solid HAN. However, if more nitric acid is added, the precipitate dissolves before the stoichiometric amount of acid has been added. Therefore, sufficient nitric acid is added to form a maximum amount of solid HAN precipitate. The solid HAN is then isolated by conventional means such as filtration or centrifugation, possibly preceded by chilling this solution. The excess alcoholic solution of unreacted hydroxylamine may be recycled and used as starting material in the process.Type: GrantFiled: October 12, 2000Date of Patent: July 10, 2001Assignee: The United States of America as represented by the Secretary of the NavyInventor: Kerry L. Wagaman
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Patent number: 6255489Abstract: The invention relates to a method for producing N-acylated (hetero)aromatic hydroxylamine derivatives of formula (I), wherein the substituents, the ring atom and the index have the meanings give in the Description, by hydrogenating a (hetero)aromatic nitro-compound of general formula (II) in the presence of a hydrogenation catalyst.Type: GrantFiled: February 29, 2000Date of Patent: July 3, 2001Assignee: BASF AktiengesellschaftInventors: Ralf Klintz, Norbert Götz, Michael Keil, Manfred Heilig, Horst Wingert, Uwe Josef Vogelbacher, Josef Wahl, Frank Wetterich, Gregor Daun
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Patent number: 6229048Abstract: A method for treating cancer comprising administering a 1,3,4,6-tetrahydroxy-helianthrone derivative. The compounds can be used in the absence of light irradiation or for photodynamic therapy of solid tumors wherein the tumor site is subjected to light irradiation after administration of the active ingredient. A preferred compound is 10,13-dimethyl-1,3,4,6-tetrahydroxy-helianthrone.Type: GrantFiled: January 31, 2000Date of Patent: May 8, 2001Assignees: Yeda Research and Development Co. Ltd. at the Weizmann Institute of Science, New York UniversityInventors: Yehuda Mazur, Gad Lavie
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Patent number: 6218536Abstract: 1,2-Bis-adducts of stable hindered nitroxide compounds with substituted ethylenes are prepared by reacting two equivalents of nitroxyl compound with an ethylenically unsaturated compound such as styrene or an acrylate ester. These adducts are very effective inhibitors to prevent the premature polymerization of ethylenically unsaturated monomers when such monomers are distilled, processed or stored.Type: GrantFiled: October 7, 1998Date of Patent: April 17, 2001Assignee: Ciba Specialty Chemcials CorporationInventors: Glen Thomas Cunkle, Thomas F. Thompson, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 6211410Abstract: According to the inventive method for producing organic hydroxylamines, at least one organic nitro compound is partially hydrogenated in the presence of an organic base or ammonia, a trivalent phosphor compound and a hydrogenation catalyst. The invention is characterised in that quantities of the nitrogen base of more than 10 wt. % in relation to the organic nitro compound are used.Type: GrantFiled: May 22, 2000Date of Patent: April 3, 2001Assignee: Consortium für elektrochemische Industrie GmbHInventors: Johannes Freudenreich, Jürgen Stohrer
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Patent number: 6197825Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.Type: GrantFiled: May 28, 1998Date of Patent: March 6, 2001Assignee: Florida International UniversityInventor: David Alan Becker
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Patent number: 6197826Abstract: Disclosed are novel &agr;-(2-hydroxyphenyl) nitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for inflammation-related conditions in mammals, such as arthritis, and as analytical reagents for detecting free radicals.Type: GrantFiled: July 16, 1999Date of Patent: March 6, 2001Assignee: Centaur Pharmaceuticals, Inc.Inventors: L. David Waterbury, John M. Carney, Allan L. Wilcox
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Patent number: 6194598Abstract: Nucleotide compositions containing aminooxy moieties are provided. In accordance with preferred embodiments, oligonucleotides and oligonucleotide analogs are provided which are specifically hybridizable with a selected sequence of RNA or DNA wherein at least one of the nucleoside moieties of the oligonucleotide is modified to include an aminooxy moiety.Type: GrantFiled: January 5, 2000Date of Patent: February 27, 2001Assignee: ISIS Pharmaceuticals, Inc.Inventors: Phillip Dan Cook, Muthiah Manoharan, Andrew Mamoru Kawasaki
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Patent number: 6194461Abstract: A compound represented by the figure (1) or a pharmaceutically acceptable salt thereof is useful as medicament for treating retinal degenerative disorders: wherein Ar is optionally substitued phenyl or optionally substituted heteroaryl;. n is 0, 1 or 2; W is —CH2NH— or —CH═N(O)—; R1, R2 and R3 are independently optionally substituted alkyl, carboxyl or alkoxycarbonyl; any two groups of R1, R2 and R3 may be taken together with the carbon atom to form optionally substituted cycloalkane; all of R1, R2 and R3 may be taken together with the adjusent carbon atom to form optionally substituted bicycloalkane or optionally substituted tricycloalkane; R4 and R5 are independently hydrogen atom or optionally substituted alkyl.Type: GrantFiled: March 15, 1999Date of Patent: February 27, 2001Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Kazuhito Ikeda, Tohru Tatsuno, Hiroki Ogo, Shuji Masumoto, Tatsuya Fujibayashi, Ryu Nagata
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Patent number: 6166256Abstract: The present invention provides a process for preparing (4-nitroso-phenyl)phenyl-hydroxylamine which is characterized in that nitrobenzene is reacted in the presence of hydroxide and/or oxide-containing bases, optionally in the presence of solvents, at temperatures of 20 to 180.degree. C. and pressures of 0.1 to 10 bar.The process according to the invention has the particular advantage that it uses inexpensive and cost-effective nitrobenzene as starting material instead of the nitrosobenzene conventionally used hitherto.Type: GrantFiled: May 8, 2000Date of Patent: December 26, 2000Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Carl Casser, Pieter Ooms, Michael Schelhaas, Christian Laue, Michaela Meiers, Gerhard Braun
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Patent number: 6106797Abstract: The present invention relates to a gauze catalyst based on titanium or vanadium zeolites and inert gauze fabrics which is suitable for accelerating oxidation reactions such as epoxidation of olefins, hydrogen peroxide production or hydroxylamine synthesis.Type: GrantFiled: August 26, 1998Date of Patent: August 22, 2000Assignee: BASF AktiengesellschaftInventors: Ulrich Muller, Franz Josef Brocker, Georg Heinrich Grosch, Hermann Putter, Michael Schulz, Norbert Rieber, Wolfgang Harder
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Patent number: 6057269Abstract: Benzylhydroxylamines I ##STR1## (X=--N(R.sup.7)--O--; Y=O, S; R.sup.1 =halogen, CN, NO.sub.2, CF.sub.3 ; R.sup.2 =H, halogen; R.sup.3 =H, NH.sub.2, CH.sub.3 ;R.sup.4 =H, halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -alkylsulfinyl or C.sub.1 -C.sub.6 -alkylsulfonyl;R.sup.5 =H, halogen, C.sub.1 -C.sub.6 -alkyl;R.sup.6 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.2 -C.sub.6 -alkenyl;R.sup.7 =H, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.6 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.1 -C.sub.6 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.2 -C.sub.8 -alkenyloxycarbonyl, C.sub.2 -C.sub.6 -alkynyloxycarbonyl, C.sub.1 -C.sub.6 -alkylthiocarbonyl, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.Type: GrantFiled: January 5, 1998Date of Patent: May 2, 2000Assignee: BASF AktiengesellschaftInventors: Ralf Klintz, Gerhard Hamprecht, Elisabeth Heistracher, Peter Schafer, Cyrill Zagar, Karl-Otto Westphalen, Helmut Walter, Ulf Misslitz, Olaf Menke, Markus Menges
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Patent number: 6046232Abstract: Disclosed are novel .alpha.-aryl-N-alkylnitrone compounds and pharmaceutical compositions containing such compounds. The disclosed compositions are useful as therapeutics for preventing and/or treating neurodegenerative, autoimmune and inflammatory conditions in mammals and as analytical reagents for detecting free radicals.Type: GrantFiled: October 15, 1998Date of Patent: April 4, 2000Assignee: Centaur Pharmaceuticals, Inc.Inventors: Judith A. Kelleher, Kirk R. Maples, Alina Dykman, Yong-Kang Zhang, Allan L. Wilcox, Julian Levell
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Patent number: 6037361Abstract: Fluorinated butyric acid compounds and derivatives are described as well as acid methods for the preparation and pharmaceutical compositions of same, which are useful as inhibitors of matrix metalloproteinases, particularly gelatinase A (72 kD gelatinase) and stromelysin-1, and also collagenase, matrilysin, and MMP-13, and for the treatment of multiple sclerosis, atherosclerotic plaque rupture, aortic aneurism, heart failure, restenosis, periodontal disease, corneal ulceration, treatment of burns, decubital ulcers, wound healing, cancer, inflammation, pain, arthritis, or other autoimmune or inflammatory disorders dependent upon tissue invasion by leukocytes or other activated migrating cells, acute and chronic neurodegenerative disorders including stroke, head trauma, spinal cord injury, Alzheimer's disease, amyotrophic lateral sclerosis, cerebral amyloid angiopathy, AIDS, Parkinson's disease, Huntington's disease, prion diseases, myasthenia gravis, and Duchenne's muscular dystrophy.Type: GrantFiled: March 9, 1998Date of Patent: March 14, 2000Assignee: Warner-Lambert CompanyInventors: Bruce David Roth, Patrick Michael O'Brien, Drago Robert Sliskovic
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Patent number: 6037377Abstract: Compounds of the formula ##STR1## which is explained more fully in the specification, may be prepared by conventional methods and used therapeutically in conventional galenic preparations.Type: GrantFiled: June 5, 1995Date of Patent: March 14, 2000Assignee: Boehringer Ingelheim KGInventors: Ralf Anderskewitz, Kurt Schromm, Ernst-Otto Renth, Frank Himmelsbach, Franz Birke, Armin Fugner
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Patent number: 6034274Abstract: The present invention relates to a proccss for preparing cis-(1S)-N-methyl-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphtalenami ne and its acid addition salts wherein N-methyl-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphtalene-1-en]-amine -N-oxide is hydrogenated in an inert solvent in the presence of a catalyst, then the resulting mixture is treated with alcanolic solution of a mineral acid, the resulting cis-racemic acid addition salt is converted to the free base by known methods, resolved and the resulting cis-(+)-base of formula (II) is converted to an acid addition salt. N-methyl-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphtalene-1-en]amine- N-oxide is also disclosed.Type: GrantFiled: July 27, 1999Date of Patent: March 7, 2000Assignee: Richter GedeonInventors: Krisztina Vukics, Tamas Fodor, Janos Fischer, Iren Fellegvari, Sandor Levai
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Patent number: 6031130Abstract: A method for preparing N,N-disubstituted hydroxylamine compounds represented by the formula (II): HO--N(R.sup.1)(R.sup.2) wherein R.sup.1 and R.sup.2 may be the same or different, and independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aromatic heterocyclic group, which comprises the step of adding a rhenium catalyst and aqueous hydrogen peroxide to a mixture containing a secondary amine compound represented by the formula (I): HN(R.sup.1)(R.sup.2) wherein R.sup.1 and R.sup.2 have the same meanings as those defined above and a dehydrating agent.Type: GrantFiled: May 21, 1998Date of Patent: February 29, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Masuji Motoki, Tadahisa Sato
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Process for producing substituted amines and a method for purifying synthetic intermediates therefor
Patent number: 5932759Abstract: The present invention relates to a process for producing a substituted amine represented by the general formula (IV):R.sup.2 NHOR.sup.3 (IV)(wherein R.sup.2 represents a hydrogen atom, a hydrocarbon group or a heteroatom-containing hydrocarbon group, and R.sup.3 represents a hydrocarbon group or a heteroatom-containing hydrocarbon group), which comprises the steps of:(b) reacting a hydroxamic acid represented by the general formula (II):R.sup.1 CONHOH (II)(wherein R.sup.1 represents a hydrogen atom or a hydrocarbon group) in the presence of a base with a reaction reagent capable of introducing a hydrocarbon or a heteroatom-containing hydrocarbon group to an oxygen atom and/or a nitrogen atom to form a substituted hydroxamic acid represented by the general formula (III): ##STR1## (wherein R.sup.1, R.sup.2 and R.sup.Type: GrantFiled: February 13, 1997Date of Patent: August 3, 1999Assignee: Mitsui Chemicals, Inc.Inventors: Yoshio Motoyama, Naoshi Nagai, Takeshi Ishitoku, Noriaki Kihara -
Patent number: 5932620Abstract: A 1,2-ethanediol derivative represented by the general formula ?I! or its salt: ##STR1## has a NGF activity-potentiating effect and is useful as a remedy for various diseases caused by degeneration of central nervous system or peripheral nervous system such as senile dementia of Alzheimer type, Huntington's chorea, various neuropathies, Riley-Day syndrome, traumatic nerve injury, amyotrophic lateral sclerosis (ALS) and the like.Type: GrantFiled: December 31, 1997Date of Patent: August 3, 1999Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Mutsuko Maekawa, Kazunari Hirata, Hirokazu Narita
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Patent number: 5910549Abstract: An improved process for free radical polymerization is produced making it possible to control the growth steps of a polymerization to produce homopolymers and copolymers, including block and graft copolymers. The process uses a long half-life radical initiators and compounds which have the structure of formula I ##STR1## wherein X is a group having at least one carbon atom and is such that the free radical X is capable of polymerizing the unsaturated monomer by free radical polymerization, and the radical functionality resides on the or one of the carbon atoms, R.sup.1, R.sup.2, R.sup.5 and R.sup.6 represent the same or different straight chain or branched substituted or unsubstituted alkyl groups of a chain length sufficient to provide steric hindrance and weakening of the O--X bond, and R.sup.3 and R.sup.4 represent the same or different, straight chain or branched, substituted alkyl groups or R.sup.3 CNCR.sup.Type: GrantFiled: August 22, 1996Date of Patent: June 8, 1999Assignee: Carnegie-Mellon UniversityInventors: Krzysztof Matyjaszewski, Dorota Greszta
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Patent number: 5891916Abstract: A compound represented by the formula: ##STR1## wherein Ar.sup.1 and Ar.sup.2 independently represent an optionally substituted aromatic group; Q represents an optionally substituted divalent aliphatic hydrocarbon group optionally containing O or S; R.sup.1 represents H, acyl group, etc.; and X represents an electron-withdrawing group, an optionally substituted aromatic group, a group of the formula: ##STR2## wherein R.sup.2 and R.sup.3 independently represent H, acyl group or an optionally substituted hydrocarbon group, etc., etc.; or salts thereof are useful as an excellent anti-neurodegenerative agent.Type: GrantFiled: June 14, 1996Date of Patent: April 6, 1999Assignee: Takeda Chemical Industries, Ltd.Inventors: Kaneyoshi Kato, Yoshihiro Sugiura, Ken-ichi Naruo, Hideki Takahashi
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Patent number: 5852215Abstract: Aromatic azomethines are produced by continuous reaction of an aniline with a formaldehyde source, with continuous evaporation to remove residual water of reaction. The azomethine product may be further reacted, either continuously or in batch process, with a haloacetylating agent, and, additionally, with an aliphatic alcohol.Type: GrantFiled: September 19, 1996Date of Patent: December 22, 1998Assignee: Zeneca LimitedInventors: Kambiz Javdani, Louie A. Nady, Ping H. Sih, Gilbert Rodriguez
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Patent number: 5840984Abstract: Odor formation during storage of (hydrocarbylthio)aromatic amines due to formation and release of odoriferous sulfur-containing species such as dihydrocarbyldisulfides, is suppressed. To accomplish this, a small amount of N,N-dihydrocarbylhydroxylamine odor-inhibitor (e.g., N,N-diethylhydroxylamine) is blended with the (hydrocarbylthio)aromatic amine. This enables products such as a mixture of 3,5-di(methylthio)-2,4-diaminotoluene and 3,5-di(methylthio)-2,6-diaminotoluene) to be stored for long periods of time with significantly reduced formation and release of odoriferous sulfur-containing species.Type: GrantFiled: June 23, 1997Date of Patent: November 24, 1998Assignee: Albemarle CorporationInventors: Gregory H. Lambeth, Paul L. Wiggins, William R. Brown
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Patent number: 5831093Abstract: A process for preparing aromatic or heteroaromatic hydroxylamines of the general formula I ##STR1## where R.sup.1 is an unsubstituted or substituted aryl radical or an unsubstituted or substituted hetaryl radical from the pyridine or quinoline groups, by hydrogenation of nitro compounds of the general formula IIR.sup.1 --NO.sub.2 (II)where R.sup.1 has the meaning indicated above, in the presence of a platinum catalyst on an activated carbon support or in the presence of a palladium catalyst doped with sulfur or selenium on an activated carbon support, by carrying out the reaction in the presence of a nitrogen-substituted morpholine compound of the general formula III ##STR2## R.sup.2 being alkyl radicals having 1 to 5 carbon atoms and R.sup.3 to R.sup.10 being hydrogen atoms or alkyl radicals having 1 to 5 carbon atoms is described.Type: GrantFiled: July 7, 1997Date of Patent: November 3, 1998Assignee: BASF AktiengeseschaftInventors: Norbert Gotz, Bernd Muller, Hubert Sauter, Joachim Gebhardt, Oliver Wagner
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Patent number: 5811579Abstract: The present invention relates to a method of synthesizing a 2-substituted nitrogen containing compound having a formula (I): ##STR1## by reacting a hydroxylamine of formula (II); ##STR2## or a nitrone of formula (III): ##STR3## with a compound of formula (IV); ##STR4## thereby to form an intermediate compound, and thereafter causing or allowing said intermediate compound to undergo a pericyclic sigmatropic rearrangement reaction to form the compound (I); wherein X is a nucleofugal group, Y is selected from O,S,NH,NR.sub.5 and CR.sub.6 R.sub.7, R.sub.1 is a group which directs the reactivity of compound (II) on to the oxygen atom and R.sub.2 to R.sub.9 are each a substituted or unsubstituted aliphatic, aromatic, heteroaryl or cyclic group or hydrogen which is substantially inert or is protected during the reaction.Type: GrantFiled: May 7, 1997Date of Patent: September 22, 1998Assignee: Eastman Kodak CompanyInventor: John DeMita Goddard
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Patent number: 5808150Abstract: The invention provides a stabilized aqueous, semi-aqueous, or non-aqueous solution of hydroxylamine or a partially neutralized hydroxylamine salt and a process therefore. The invention utilizes as a stabilizing agent a specific acetic acid compound.Type: GrantFiled: August 14, 1997Date of Patent: September 15, 1998Assignee: Concept Sciences, Inc.Inventor: Frank Michelotti
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Patent number: 5780257Abstract: Method for detecting peroxidase or hydrogen peroxide with high sensitivity. Both peroxidase and hydrogen peroxide are prepared such that one of them is overabundant to the other. Phenoxy radicals are produced from a p-substituted phenol compound by the action of peroxidase in the presence of hydrogen peroxide. The free radicals are trapped by a hydroxy amine compound, and stable radical species are produced. Electron spin resonances of the stable radical species are measured.Type: GrantFiled: July 18, 1996Date of Patent: July 14, 1998Assignees: Yamagata Technopolis Foundation, JEOL Ltd.Inventors: Masaaki Aoyama, Masanobu Shiga
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Patent number: 5777164Abstract: The present invention discloses a method comprising the steps of;a) forming in an aqueous solution a hydroxamic acid from a hydroxylamine free base and anhydride having the formula (RCO).sub.2 O wherein R is H or a substituted or unsubstituted C.sub.2-6 alkyl, C.sub.2-6 alkenyl, C.sub.6-10 aryl, or C.sub.4-10 heteroaryl; andb) treating said hydroxamic acid with an alkylating agent in the presence of at least one proton scavenger under conditions sufficient to consume substantially all of said alkylating agent to form an O-substituted hydroxamate.The protection and alkylation are readily effected in water (with no alcohol co-solvent) without the need for phase-transfer catalysis and with little hydrolysis of the alkylating agent.Type: GrantFiled: April 14, 1997Date of Patent: July 7, 1998Assignee: Eastman Chemical CompanyInventor: Neil Warren Boaz
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Patent number: 5777163Abstract: Hydroxylamines are prepared from ammonia or the corresponding amines, hydrogen and oxygen by a process in which the starting materials are reacted under heterogeneous catalysis using an oxidation catalyst based on a titanium or vanadium silicalite having a zeolite structure and containing from 0.01 to 20% by weight of one or more platinum metals selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum, the platinum metals each being present in at least two different bond energy states.Type: GrantFiled: April 4, 1997Date of Patent: July 7, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Muller, Daniel Heineke
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Patent number: RE36594Abstract: The invention is the use of nitronyl substituted hindered phenols as antioxidants in therapeutic applications. In the preferred embodiment the compositions have the general formula: ##STR1## Wherein R1 is hydrogen, an alkyl or an aryl and R2 is an alkyl or an aryl; R.sub.3 is an alkyl; and R.sub.4 is an alkyl. Further, the invention relates to novel compositions useful as antioxidants. The novel compounds include: 2,6-di-tert-butyl-4-(N-tert-octyl)nitronyl phenol (DBONP); 2,6-dimethyl-4-(N-tert-octyl)nitronyl phenol (DMONP); N-tert-octyl-C-phenyl nitrone (OPN).Type: GrantFiled: October 2, 1997Date of Patent: February 29, 2000Assignee: Oklahoma Medical Research FoundationInventors: Edward G. Janzen, Allan L. Wilcox