Additional Amino Nitrogen Containing Patents (Class 564/434)
  • Publication number: 20020156311
    Abstract: Compounds of formula (I) 1
    Type: Application
    Filed: February 8, 2002
    Publication date: October 24, 2002
    Inventors: James T. Link, Bryan K. Sorensen, Jyoti R. Patel, David L. Arendsen, Gaoquan Li
  • Patent number: 6433021
    Abstract: Indane compounds of general formulae (1) to (4) and their pharmaceutical use, particularly to achieve mast cell stabilising activity and/or anti-inflammatory activity are described.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: August 13, 2002
    Assignee: Venantius Limited
    Inventors: Neil Frankish, Helen Sheridan, John Walsh, Michael Jordan
  • Patent number: 6426324
    Abstract: An antioxidant composition suitable for ester fluid lubricants is the reaction product of diphenylamine and N-aryl naphthylamine in the presence of an organic peroxide. The mole ratio of diphenylamine:N-aryl naphthylamine is about 1:1 to about 10:1. This results in more oligomeric reaction products and significantly less unreacted monomeric residual reactants. The resultant product composition comprises DPA homo-oligomers and DPA-NPA cross oligomers. The diphenylamine and N-aryl naphthylamine are desirably substituted with alkyl groups having from 1 to 20 carbon atoms or styryl groups. The reaction temperature is preferably about 130° to about 150° C. Controlled reaction conditions allow the use of solvents with extractable hydrogen atoms without producing significant amounts of dehydrocondensation between the solvent and the diamines.
    Type: Grant
    Filed: October 25, 2000
    Date of Patent: July 30, 2002
    Assignees: Noveon IP Holdings Corp., BP Exploration & Oil, Inc.
    Inventors: John Ta-Yuan Lai, Deborah S. Filla
  • Publication number: 20020094452
    Abstract: An electro-luminescent element comprising an organic compound layer is disclosed.
    Type: Application
    Filed: September 24, 2001
    Publication date: July 18, 2002
    Inventors: Noriko Ueda, Mitsunori Matsuura, Hiroshi Kita
  • Patent number: 6395933
    Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst. Certain phase transfer catalysts may also function as the strong base.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: May 28, 2002
    Assignee: Flexsys America, L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Publication number: 20020055652
    Abstract: The invention provides a process for preparing 4-aminodiphenylamine, an important starting product for synthesizing antioxidants and stabilizers in the rubber and polymer industry, by hydrogenating nitrosobenzene with hydrogen in the presence of a proton acid as catalyst and in the presence of a hydrogenating catalyst, optionally in the presence of an inert organic solvent and thermally decomposing the 4-ADPA ammonium salt produced in this way, wherein 4-ADPA is obtained.
    Type: Application
    Filed: November 6, 2001
    Publication date: May 9, 2002
    Inventors: Michael Schelhaas, Carl Casser, Dietmar Bielefeldt, Pieter OOms, Joachim Haider, Manfred Jautelat, Christian Laue, Henry Giera
  • Publication number: 20020016508
    Abstract: A phenylenediamine derivative represented by following formula (I) or (II): 1
    Type: Application
    Filed: August 2, 2001
    Publication date: February 7, 2002
    Applicant: NOK Corporation
    Inventors: Seiji Nakagome, Akihiko Toda
  • Patent number: 6342637
    Abstract: A novel diamine compound of formula (I) of the present invention having a high glass transition temperature is useful as an improved hole transport agent, and an organic electroluminescent device containing the diamine compound of formula (I) has good thermal and mechanical stabilities, and prolonged lifetime.
    Type: Grant
    Filed: August 9, 2001
    Date of Patent: January 29, 2002
    Assignee: Nessdisplay Co., Ltd.
    Inventors: Ki-jong Han, Youngkoo Kim, Jae-Gyoung Lee, Dong-Kwon Choi
  • Patent number: 6338927
    Abstract: The present invention relates to a novel stilbene derivative, which is a stilbene compound wherein molecular structures of triphenylamino groups located at both sides of a benzene ring in a molecular center are unsymmetric, and an electrophotosensitive material having high sensitivity and improved repeatability, comprising a conductive substrate and a photosensitive layer formed on the substrate, the photosensitive layer containing the derivative.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: January 15, 2002
    Assignee: Kyocera Mita Corporation
    Inventors: Yoshio Inagaki, Yukimasa Watanabe
  • Patent number: 6337167
    Abstract: To provide compounds, which are suitable for use as an organic luminescent material capable of developing intense luminescence which is yellow to red, and a process for preparing in general and high efficiency. A bis(aminostyryl)benzene compound of the following general formula [I] is provided wherein R2 and R3 independently represent an unsubstituted aryl group, and R1 and R4 independently represent an aryl group, and R5 to R8, independently represent a cyano group or the like. A process for the preparation thereof is described wherein a 4-(N,N-diarylamino)benzaldehyde and a diphosphonic acid ester or diphosphonium are subjected to condensation reaction. Intermediates of the bis(aminostyryl)benzene compound are also described.
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: January 8, 2002
    Assignee: Sony Corporation
    Inventors: Mari Ichimura, Shinichiro Tamura, Tadashi Ishibashi, Ichinori Takada
  • Publication number: 20010046612
    Abstract: A hole transporting compound for organic electroluminescent devices with good thermal stability, which includes 6,6′-bis(9H,9-carbazolyl)-N,N′-disubstituted-3,3′-bicarbazyl as a basic molecular structure, is represented by the following formula I: 1
    Type: Application
    Filed: February 8, 2001
    Publication date: November 29, 2001
    Applicant: Samsung SDI Co., Ltd.
    Inventors: Ji-Hoon Lee, In-Seo Kee, Sung-Woo Cho, Byung-Hoon Chae
  • Patent number: 6177220
    Abstract: Disclosed are a stilbene derivative having the general formula (1) and a production thereof, and the electrophotosensitive material comprises a conductive substrate and a photosensitive layer provided on the conductive substrate, wherein the photosensitive layer contains a stilbene derivative (1): wherein R1 and R3 represent an alkyl group which may have a substituent, an alkoxy group which may have a substituent or the like, and R2 and R4 represent a hydrogen atom, an alkyl group which may have a substituent or the like.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: January 23, 2001
    Assignee: Kyocera Mita Corporation
    Inventors: Yukimasa Watanabe, Hirofumi Kawaguchi
  • Patent number: 6172264
    Abstract: A triphenylamine derivative, represented by the following general formula (1): wherein R1, R2, R3, R4, R5 and R6 each represents a hydrogen atom, a lower alkyl group, an alkoxy group, a halogen atom or an aryl group which may have a substituent group; and m and n each represents 0 or 1.
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: January 9, 2001
    Assignee: Takasago International Corporation
    Inventors: Tohru Kobayashi, Yoshimasa Matsushima, Hiroshi Sugiyama, Toshimitsu Hagiwara
  • Patent number: 6160177
    Abstract: Oligomeric anilines (I; n=2, 4), useful in sensors for volatile organic compounds, in corrosion-resistant coatings for metals and metal alloys, and in applications which use electroactive materials, are prepared. Thus, tetraaniline in the emeraldine oxidation. state (n=1) was prepared by the ferric chloride-promoted oxidative coupling of N-phenyl-1,4-phenylenediamine HCl salt and recrystallizing the reaction mixture from PhMe, and next converted to tetraaniline in the leucoemeraldine oxidation state by treatment with hydrazine. Tetraaniline in the leucoemeraldine oxidation state was then contacted with an oxidative coupling agent (e.g., ammonium peroxydisulfate) to produce aniline oligomers I (n=2 and 4).
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: December 12, 2000
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Alan G. MacDiarmid, Jing Feng, Wanjin Zhang
  • Patent number: 6100430
    Abstract: An alicyclic polyamine of the formula (1) ##STR1## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group and R.sub.1 through R.sub.4 are the same or different and each represents hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. The alicyclic polyamine can be obtained by subjecting a 3-formylcycloalkanone or 3-formylcycloalkenone to reductive amination reaction.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: August 8, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
  • Patent number: 6096927
    Abstract: A process for recovery of N,N'-bis(alkylphenyl)-[1,1'-biphenyl]-4,4'-diamine from an electrophotographic imaging member, the process includingproviding an electrophotographic imaging member including at least one imaging layer, the imaging layer including a film forming binder and N,N'-bis(alkylphenyl)[1,1'-biphenyl]-4,4'-diamine,contacting the at least one imaging layer with warm toluene to dissolve toluene soluble materials including the film forming binder and N,N'-bis(alkylphenyl)-[1,1'-biphenyl]-4,4'-diamine to form a mixture containing undissolved material and a solution of toluene and the toluene soluble materials,isolating the solution from the undissolved material,concentrating the solution in a partial vacuum and with applied heat,cooling the concentrate,mixing the concentrate with acetone to precipitate the N,N'-bis(alkylphenyl)-[1,1'-biphenyl]-4,4'-diamine,separating the N,N'-bis(alkylphenyl)-[1,1'-biphenyl]-4,4'-diamine precipitate from the concentrate,washing the N,N'-bis(alkylphenyl)-[1,1'-biph
    Type: Grant
    Filed: August 2, 1999
    Date of Patent: August 1, 2000
    Assignee: Xerox Corporation
    Inventors: Satish R. Parikh, Edward J. Radigan, Jr., Anthony M. Horgan, John A. Bergfjord, Sr.
  • Patent number: 6093853
    Abstract: A phenylenediamine derivative represented by following formula (I) or (II): ##STR1## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; R.sub.3 represents a hydrogen atom or a methyl group; R.sub.4 represents a methyl group or an ethyl group; and n and m each is 1, 2, or 3; ##STR2## wherein R.sub.1 and R.sub.2 each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a cyano group; and n and m each is 1, 2, or 3, is disclosed.These phenylenediamine derivatives are effectively used as antioxidants for rubbers, which scarcely cause vanishing by evaporation or a thermal denaturation even under a high-temperature condition of 150.degree. C. or higher.
    Type: Grant
    Filed: June 30, 1998
    Date of Patent: July 25, 2000
    Assignee: NOK Corporation
    Inventors: Seiji Nakagome, Akihiko Toda
  • Patent number: 6090985
    Abstract: The present invention generally describes novel chiral polyanilines in their doped (protonated) forms and novel methods for their chemical synthesis comprising polymerizing an aniline monomer in the presence of a chiral dopant acid, an oxidizing agent, and, optionally, a substrate, and their conversion by treatment with a base to novel chiral polyanilines in their de-doped base forms. The novel chiral polyanilines of the present invention may be used as electrodes for asymmetric synthesis, as biological sensors and as separation materials in pharmaceutical applications.
    Type: Grant
    Filed: June 28, 1999
    Date of Patent: July 18, 2000
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Alan G. MacDiarmid, Leon A. P. Kane-Maguire, Weigong Zheng, Gordon G. Wallace, Ian D. Norris
  • Patent number: 6074734
    Abstract: The present invention provides a triamine compound represented by general formula (I): ##STR1## an organic luminescence device which comprises an organic layer and a pair of electrodes disposed on both sides of the organic layer wherein the organic layer at least contains a layer of a light emitting zone and a layer of a hole transporting zone which comprises a hole injecting layer containing the triamine compound and a hole transporting layer, and an organic thin film comprising two layers which are a layer containing a compound represented by general formula (I) and having a thickness of 5 nm to 5 .mu.
    Type: Grant
    Filed: July 21, 1997
    Date of Patent: June 13, 2000
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hisayuki Kawamura, Hiroaki Nakamura, Chishio Hosokawa
  • Patent number: 6069279
    Abstract: A method for the preparation of aromatic amines such as N-phenyl-p-phenylenediamine wherein an aromatic amine such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of a metal pentacyano ferrate(II) complex, includes subsequent catalytic reduction of the complex by hydrogenation in the presence of a metal catalyst having at least two Group VIII metals, preferably platinum in combination with ruthenium either together on a single carbon support or each metal separately on carbon supports.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: May 30, 2000
    Inventors: Mark W. Simon, Mohammad A. Khan
  • Patent number: 6022998
    Abstract: The present invention provides a novel stilbene derivative represented by the general formula (1): ##STR1## wherein R.sup.1 and R.sup.3 represent an alkyl group, an aryl group, an aralkyl group or an alkoxy group which are optionally substituted; and R.sup.2 and R.sup.4 represent a hydrogen atom, an alkyl group or an alkoxy group which are optionally substituted, provided that when the substitution position of R.sup.2 and R.sup.4 is the 4-(para) position, R.sup.2 and R.sup.4 are hydrogen atoms, a method for producing the same and use thereof. The above stilbene derivative (1) is useful as an electric charge transferring material, particularly hole transferring material.
    Type: Grant
    Filed: July 20, 1998
    Date of Patent: February 8, 2000
    Assignee: Mita Industrial Co., Ltd.
    Inventors: Hirofumi Kawaguchi, Yukimasa Watanabe, Yoshio Inagaki
  • Patent number: 5994584
    Abstract: 4-Aminodiphenylamines are prepared by hydrogenating nitrosobenzene or mixtures of nitrosobenzene and nitrobenzene with hydrogen in the presence of fluorides and heterogeneous catalysts in inert aprotic solvents at temperatures from 0 to 200.degree. C. and pressures from 0.1 to 150 bar.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: November 30, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Henrey Giera
  • Patent number: 5985880
    Abstract: A method of reducing, treating or preventing drug-mediated respiratory depression in an animal, incident to the administration to said animal of a respiratory depression-mediating drug, comprising administering to the animal receiving said drug an effective amount of a .delta. receptor agonist compound.
    Type: Grant
    Filed: July 3, 1997
    Date of Patent: November 16, 1999
    Assignee: Delta Pharmaceuticals
    Inventors: Kwen-Jen Chang, Robert W. McNutt, Jr., Hugh O. Pettit, Michael J. Bishop
  • Patent number: 5977411
    Abstract: This invention provides a method for preparing 4-ADPA by charging nitrobenzene into a reaction zone under hydrogen pressure in the presence of a strong organic base and a catalyst for hydrogenation. The method provides the convenience and economy of a one-step process, while producing improved yields and selectivities. The invention further provides for various embodiments of the foregoing which are suitable for the production of 4-ADPA, and the hydrogenation or reductive alkylation to produce PPD. Important to the invention are the molar ratios of aniline to nitrobenzene and nitrobenzene to the strong organic base and the choice and use of hydrogenation catalyst.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: November 2, 1999
    Assignee: Flexsys America L.P.
    Inventor: Antonio L. DeVera
  • Patent number: 5945554
    Abstract: A process for the stabilizing of an organosilane with an effective, stabilizing amount of purified N,N'-diphenyl-p-phenylenediamine (DPPD). The purification of crude DPPD involves extracting crude DPPD with hexane thereby forming an extract solution containing DPPD, passing the extract solution over an adsorption layer comprising silica gel as the adsorbent to form a solution containing purified DPPD and recovering the purified DPPD from the solution.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: August 31, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Albert-Johannes Frings, Michael Horn, Peter Jenker, Jaroslaw Monkiewicz, Hans-Guenther Srebny, Burkhard Standke, Bertram Trautvetter
  • Patent number: 5932768
    Abstract: 4-aminodiphenylamines are prepared by hydrogenating nitrosobenzene or mixtures of nitrosobenzene and nitrobenzene with hydrogen in the presence of bases containing hydroxide, oxide and/or alkoxide groups and heterogeneous catalysts in inert aprotic solvents at temperatures of from 0 to 200.degree. C. and at pressures of from 0.1 to 150 bar.
    Type: Grant
    Filed: July 30, 1998
    Date of Patent: August 3, 1999
    Assignee: Bayer AG
    Inventors: Pieter Ooms, Ulrich Notheis, Christian Laue
  • Patent number: 5925791
    Abstract: 4-aminodiphenylamines are produced by hydrogenating nitrobenzene with hydrogen in the presence of bases containing hydroxide and/or oxide groups and heterogeneous catalysts and in the presence of inert aprotic solvents at temperatures of 0 to 200.degree. C. and pressures of 0.1 to 150 bars.
    Type: Grant
    Filed: February 27, 1998
    Date of Patent: July 20, 1999
    Assignee: Bayer AG
    Inventors: Hans-Josef Buysch, Christian Laue, Heinrich Konigshofen, Ulrich Notheis, Pieter Ooms, Ursula Pentling
  • Patent number: 5925790
    Abstract: A method for producing aromatic amines such as N-phenyl-p-phenylenediamine is disclosed wherein an amine substituted aromatic such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of a preferred trisodium pentacyano ferrate(II) complex containing various water soluble ligands, such as ammonia, mono alkyl amine, dialkyl amines, and trialkyl amines. The complex is subsequently catalytically reduced by hydrogenation using certain heterogeneous metal catalysts to yield the desired aromatic amine.
    Type: Grant
    Filed: March 13, 1997
    Date of Patent: July 20, 1999
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Edward L. Wheeler, Russell E. Malz, Jr., Mark W. Simon
  • Patent number: 5840982
    Abstract: An improvement in a process for the preparation of a p-aminodiarylamine by reduction of the corresponding nitroso or nitro compound with hydrogen in a hydrogenator in the presence of a catalyst is disclosed. The invention includes equipping the hydrogenator with filtration means capable of separating the p-aminodiarylamine product from the catalyst, whereby the p-aminodiarylamine product can be removed from the hydrogenator while the catalyst is retained therein, thereby permitting the reaction to be run semicontinuously or continuously.
    Type: Grant
    Filed: June 4, 1998
    Date of Patent: November 24, 1998
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Michael Reynolds, Russell E. Malz
  • Patent number: 5837166
    Abstract: Organic electroluminescence devices having the life of light emission superior to those of conventional electroluminescence devices, and novel arylenediamine derivatives which can remarkably improve the life of light emission of an organic electroluminescence device when the derivatives are used as a component of the device, are disclosed.The organic electroluminescence devices of the present invention at least contain a p-phenylenediamine derivative having 6 or more benzene ring skeletons, or at least a 4,4'-biphenylenediamine derivative having 5 biphenyl groups.The arylenediamine derivatives of the present invention include p-phenylenediamine derivatives having 4 biphenyl groups and 4,4'-biphenylenediamine derivatives having 5 biphenyl groups.
    Type: Grant
    Filed: March 27, 1996
    Date of Patent: November 17, 1998
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hisayuki Kawamura, Chishio Hosokawa, Tadashi Kusumoto, Hiroaki Nakamura
  • Patent number: 5773469
    Abstract: The invention relates to diaryl antimicrobial compounds of the general formula: ##STR1## where G, E L, J, q, m, X, Ar, W, p, n and A are as described herein, pharmaceutical compositions containing the compounds, methods for their production and their use in treating bacterial infections.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: June 30, 1998
    Assignee: Ortho Pharmaceutical Corporation
    Inventors: Ramesh M. Kanojia, James P. Demers, Dennis J. Hlasta, Sigmond G. Johnson, Dieter H. Klaubert
  • Patent number: 5763666
    Abstract: A process for the purification of crude N,N'-diphenyl-p-phenylenediamine (DPPD), which comprises extracting crude DPPD with a hydrocarbon or hydrocarbon mixtures thereby forming an extract solution containing DPPD, passing the extract solution over an adsorption layer, and recovering purified DPPD from the solution.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: June 9, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Albert-Johannes Frings, Michael Horn, Peter Jenker, Jaroslaw Monkiewicz, Hans-Guenther Srebny, Burkhard Standke, Bertram Trautvetter
  • Patent number: 5739403
    Abstract: 4-Aminodiphenylamines are produced by reacting optionally substituted aniline with optionally substituted nitrobenzene in the presence of water and/or alcohols and organic and/or inorganic bases and then catalytically hydrogenating the resultant nitro- and/or nitrosodiphenylamine in the presence of water, wherein the catalytic hydrogenation of the reaction mixture is performed in the presence of 25 to 80 wt. % of water, relative to the weight of the reaction mixture from the condensation reaction, the hydrogenation catalyst is removed from the hydrogenation mixture once absorption of hydrogen has ceased, 10 to 100 vol. % of aromatic solvent, relative to the total volume of the hydrogenation mixture, are optionally added to the hydrogenation mixture, the resultant organic phase is separated in order to isolate the 4-aminodiphenylamine and the aqueous phase is returned to the initial reaction mixture.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: April 14, 1998
    Assignee: Bayer AG
    Inventors: Klaus Reinartz, Adolf Brill, Fred Schuhmacher
  • Patent number: 5728882
    Abstract: A method for producing aromatic amines such as N-phenyl-p-phenylenediamine is disclosed wherein an amine substituted aromatic such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of trisodium pentacyano ferrate(II) complexes containing various water soluble ligands, such as ammonia, mono alkyl amine, dialkyl amines, and trialkyl amines. The complex is subsequently catalytically reduced by hydrogenation using certain heterogeneous metal catalysts to yield the desired aromatic amine.
    Type: Grant
    Filed: April 4, 1996
    Date of Patent: March 17, 1998
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Edward Lockwood Wheeler, Russell Edward Malz, Jr.
  • Patent number: 5689007
    Abstract: Processes of preparing para substituted phenylamines, such as, p-phenylenediamines, and particularly, p-aminodiphenylamine. One process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in specified proportions and within a specified temperature range, in the absence of oxygen, and in the presence of a homogeneous acid catalyst, such as hydrochloric acid. A second process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in the presence of a solid acid catalyst, such as acidic zeolite Y, under reaction conditions.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: November 18, 1997
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell Edward Malz, Gerard V. Smith, Mark Peter Ferrandino, Ruozhi Song, Chung-Yuan Lin, Franklin Herbert Barrows
  • Patent number: 5679680
    Abstract: The invention covers a novel series of .alpha.-substituted hydrazides that inhibit both calpain I and calpain II. They are non-peptide irreversible active site inhibitors of calpain. The compounds are useful in the treatment of neurodegenerative disorders including cerebrovascular disorders, brain injury, spinal cord, and peripheral nerve injury, cardiac infarction, cataracts, inflammation, restenosis, muscular dystrophy, and platelet aggregation. Pharmaceutical compositions, methods of using processes for preparing and novel intermediates useful in the processes are also disclosed.
    Type: Grant
    Filed: February 16, 1995
    Date of Patent: October 21, 1997
    Assignee: Warner-Lambert Company
    Inventors: Kevin Ka-Wang Wang, Po-Wai Yuen
  • Patent number: 5648538
    Abstract: A process for preparing diarylamines in high yield, in which diarylamines are prepared from arylamines in the presence of a solid acid catalyst. The solid acid catalyst with good stability and regeneration ability consists of H-type beta zeolite and active alumina, the ratio of SiO.sub.2 /Al.sub.2 O.sub.3 in the zeolite is 20.about.100, and the content of active alumina is 10%.about.70% (wt).
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: July 15, 1997
    Assignees: Fushun Research Institute of Petroleum and Petrochemicals, China Petrochemical Corp.
    Inventors: Xiusen Liu, Huarong Zhu, Fubin Ai, Lizhi Song, Zhihui Lu, Xuewei Hou
  • Patent number: 5633407
    Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: May 27, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5618979
    Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 8, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5608111
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: March 4, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
  • Patent number: 5574187
    Abstract: Processes of preparing para substituted phenylamines, such as, p-phenylenediamines, and particularly, p-aminodiphenylamine. One process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in specified proportions and within a specified temperature range, in the absence of oxygen, and in the presence of a homogeneous acid catalyst, such as hydrochloric acid. A second process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in the presence of a solid acid catalyst, such as acidic zeolite Y, under reaction conditions.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: November 12, 1996
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song, Chung-Yuan Lin, Franklin H. Barrows
  • Patent number: 5550291
    Abstract: Disclosed herein is a stereospecific synthesis amenable to the large scale preparation of a hydrochloric acid addition salt of a chlorohydrin of the formula ##STR1## wherein R.sup.1 and R.sup.2 are amino protective groups and R.sup.3 is an amino acid side chain or a protected amino acid side chain. The synthesis involves reacting an aldehyde of the formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined hereinbefore with (chloromethyl)lithium at -20.degree. C. or below and contacting the resulting diastereoisomeric mixture of lithium alcoholates with aqueous hydrochloric acid to obtain a separable mixture of the hydrochloric acid addition salts of the chlorohydrin and its corresponding hydroxy diastereoisomer. The hydrochloric acid addition salt of the chlorohydrin is transformed readily into corresponding optionally amino-protected aminoepoxides; for example, 3(S)-(tert-butyloxycarbonylamino)-l,2(S)-epoxy-4-phenyl-butane.
    Type: Grant
    Filed: May 4, 1995
    Date of Patent: August 27, 1996
    Assignee: Bio-Mega/Boehringer Ingelheim Research, Inc.
    Inventors: Pierre L. Beaulieu, Yvan Guindon, Dominik M. Wernic
  • Patent number: 5508136
    Abstract: Novel trisarylaminobenzene derivatives are represented by the formula: ##STR1## wherein .PHI..sub.11, .PHI..sub.21, and .PHI..sub.31 are independently divalent aromatic ring residues, R.sub.11, R.sub.21, and R.sub.31 are independently groups represented by --N.PHI..sub.01 .PHI..sub.02, --NH.PHI..sub.01, --NR.sub.01 .PHI..sub.01, --.PHI..sub.01, --O.PHI..sub.01 or --S.PHI..sub.01 wherein each of .PHI..sub.01 and .PHI..sub.02 is a monovalent aromatic ring residue, and R.sub.01 is an alkyl group, at least one of R.sub.11, R.sub.21, and R.sub.31 being a group represented by --N.PHI..sub.01 .PHI..sub.02, --NH.PHI..sub.01 or --NR.sub.01 .PHI..sub.01, and A.sub.12, A.sub.22, and A.sub.32 are independently aromatic residues, alkyl groups or hydrogen. An organic electroluminescent element which uses the compound in an organic compound layer, especially in a hole injection transport layer provides uniform plane light emission and is durable enough to maintain luminance.
    Type: Grant
    Filed: February 10, 1994
    Date of Patent: April 16, 1996
    Assignees: Yasuhiko Shirota, TDK Corporation
    Inventors: Yasuhiko Shirota, Kenji Nakaya, Tetsushi Inoue, Norihiro Okada, Kenryo Namba
  • Patent number: 5489711
    Abstract: An oligomer from diarylamines is disclosed which has desirable antioxidant properties in lubricating oils which contain synthetic ester lubricants. The oligomer is desirable for use at higher temperatures where it has less volatility than simple diarylamines. The oligomer has substantial portions of monosubstituted diphenylamine repeat units which result in linear oligomers. Di and polysubstituted diphenylamines may optionally be present as repeat units. These di and polysubstituted diphenylamines generally react as monofunctional reactants in oligomerization and tend to reduce the number of repeat units in the average oligomer.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: February 6, 1996
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5475139
    Abstract: This invention provides a novel process for the preparation of substituted derivatives of diphenyl amine. The special feature of this novel process is that low cost and recoverable phenolic salts are used as catalysts for molecular rearrangement and aminolysis to obtain substituted derivatives of diphenyl amine in high yield.
    Type: Grant
    Filed: October 22, 1993
    Date of Patent: December 12, 1995
    Assignee: Yung Shin Pharm. Ind. Co., Ltd.
    Inventors: Fangchen Lee, Tsung-Chung Liu
  • Patent number: 5453541
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5451702
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: April 26, 1993
    Date of Patent: September 19, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5420354
    Abstract: A process of preparing para phenylenediamines, such as, p-aminodiphenylamine. The process involves contacting nitrobenzene or a substituted derivative thereof with hydrogen and an amine, such as aniline, in the presence of a hydrogenation catalyst, a hydrogenation inhibitor, and an acid cocatalyst under reaction conditions.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: May 30, 1995
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song
  • Patent number: 5382691
    Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a substituted aromatic azo compound and an alcohol selected from the group consisting of aliphatic alcohols, cycloaliphatic alcohols, arylalkyl alcohols and mixtures thereof in the presence of a suitable base at a temperature of about 70.degree. C. to about 200.degree. C. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: January 17, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K-M. Cheng
  • Patent number: 5371289
    Abstract: The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: ##STR1## comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: ##STR2## and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula:R.sup.1 --NH.sub.2in the presence of methanol wherein R.sup.1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: December 6, 1994
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Kirkwood S. Cottman, Joseph A. Kuczkowski