Nitro Or Nitroso, Bonded Directly To Carbon, Containing Patents (Class 564/441)
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Patent number: 7250523Abstract: Compounds and processes for catalytic ring-opening cyclooligomerization metathesis and ring-closing metathesis of olefins are described. The compound is a molybdenum or tungsten metal (M) complex which comprises an imido ligand (N—R) bound to the M to provide an M=N—R site, an M=C reaction site wherein the C of the M=C reaction site is tethered to the R of the imido ligand via a carbon or carbon and heteroatom (NOS) chain containing 1 to 12 carbon atoms to form a ring structure, and two to four ligands (R?) bound to the M to provide two to four M-R? sites. In particular embodiments, the M-R? sites include each of the oxygens of a dialkoxide ligand or each of the nitrogens of an ?1-pyrrolyl ligand bound to the M.Type: GrantFiled: October 22, 2003Date of Patent: July 31, 2007Assignee: Board of Trustees of Michigan State UniversityInventors: Aaron L. Odom, James T. Ciszewski
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Patent number: 7211696Abstract: Dinitroaniline compounds useful for the treatment of diseases caused by parasitic protozoa in subjects in need of such treatment. The compounds are particularly useful in the treatment of leishmaniasis. The compounds are preferably less cytotoxic to normal cells than oryzalin. Also provided are methods of treating subjects having diseases caused by parasitic protozoa, preferably humans.Type: GrantFiled: April 23, 2003Date of Patent: May 1, 2007Assignees: The Ohio State University, National Institutes of HealthInventors: Karl Werbovetz, Dan L. Sackett, Manar M. Salem
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Patent number: 7057073Abstract: A method to convert surplus nitroarene explosives into trinitrophloroglucinol and triaminotrinitrobenzene (TATB) is described. Picric acid is directly aminated to diaminopicric acid, which is converted to trinitrophloroglucinol and triaminotrinitrobenzene.Type: GrantFiled: August 4, 2004Date of Patent: June 6, 2006Assignee: Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Michael D. Coburn, Gregory S. Lee, Robert D. Schmidt, Philip F. Pagoria, Peter C. Hsu
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Patent number: 7057072Abstract: A method to convert surplus nitroarene explosives (picric acid, ammonium picrate,) into TATB is described. The process comprises three major steps: conversion of picric acid/ammonium picrate into picramide; conversion of picramide to TATB through vicarious nucleophilic substitution (VNS) of hydrogen chemistry; and purification of TATB.Type: GrantFiled: August 2, 2004Date of Patent: June 6, 2006Assignee: The Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Michael D. Coburn, Gregory S. Lee, Robert D. Schmidt, Philip F. Pagoria, Peter C. Hsu
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Patent number: 7053123Abstract: (E)-Styryl benzylsulfones useful as antiproliferative agents, including, for example, anticancer agents, are provided according to formula I: wherein: R1 is selected from the group consisting of halogen, C1–C6 alkoxy, nitro, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); and R2 and R3 are independently selected from the group consisting of halogen, C1–C6 alkoxy, C1–C6 alkyl, nitro, cyano, hydroxyl, phosphonato, amino, sulfamyl, carboxy, acetoxy, and dimethylamino (C2–C6 alkoxy); provided: R1 may not be halogen when R2 and R3 are both halogen; R2 may not be 2-halogen when R3 is 4-halogen; or a pharmaceutically acceptable salt thereof; or formula II: wherein: R4 is selected from the group consisting of C1–C6 alkoxy, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); R6 is selected from the group consisting of nitro, hydrogen, phosphonato, amino, sulfamyl, carboxy, acetoxy and dimethylamino (C2–C6 alkoxy); and R7 is selected from the group consistinType: GrantFiled: October 5, 2001Date of Patent: May 30, 2006Assignee: Temple University-of the Commonwealth System of Higher EducationInventors: E. Premkumar Reddy, M. V. Ramana Reddy
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Patent number: 6989036Abstract: The present invention relates to novel reactive dyes of the formula (I) where R1 to R4 are independently hydrogen, C1–C8-alkyl, C2–C8-alkyl, wherein nonadjacent CH2 groups may be replaced by oxygen atoms or imino or C1–C4-alkylimino groups and/or CH2 groups by carbonyl groups, C2–C8-alkenyl, aryl, arylalkylene or a moiety containing a reactive group or the precursor of a reactive group, with the proviso that at least one of R1 to R4 is a moiety which contains a reactive group or the precursor of a reactive group. The present invention further relates to the use of the reactive dyes of the formula (I) for dyeing substrates containing nucleophilic groups and to preparations containing at least one reactive dye of the formula (I).Type: GrantFiled: April 24, 2002Date of Patent: January 24, 2006Assignee: BASF AktiengellschaftInventors: Gunter-Rudolf Schröder, Helmut Reichelt, Günther Seybold, Manfred Patsch, Stevan David Jones, James Charles Dunbar, Colin John Clarke
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Publication number: 20040215022Abstract: Disclosed are colorant compounds of the formula 1Type: ApplicationFiled: May 25, 2004Publication date: October 28, 2004Applicant: Xerox CorporationInventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
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Publication number: 20040215038Abstract: Disclosed are colorant precursor compounds of the formula 1Type: ApplicationFiled: April 24, 2003Publication date: October 28, 2004Applicant: Xerox CorporationInventors: Jeffery H. Banning, Donald R. Titterington, Clifford R. King
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Publication number: 20030204104Abstract: The present invention provides an aniline derivative represented by the formula (I) 1Type: ApplicationFiled: May 14, 2003Publication date: October 30, 2003Inventors: Masanobu Onishi, Akihiko Yoshiura, Eiji Kohno, Kenji Tsubata
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Publication number: 20030199580Abstract: This invention provides a process for the preparation of a benzimidazole derivative (I) or a pharmaceutically acceptable salt thereof, 1Type: ApplicationFiled: October 16, 2002Publication date: October 23, 2003Applicant: SANKYO COMPANY, LIMITEDInventors: Naoyuki Kishi, Yoshitaka Nakamura, Narumi Abe, Toyonori Takebayashi
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Patent number: 6630607Abstract: Aromatic methylidene compounds of the following general formula wherein R11 and R21 independently in each occurrence represent an unsubstituted or substituted alkyl or alkoxy group, a halogen, a cyano group or a nitro group, n11 and n21 are, respectively, an integer, R31 and R41 independently represent hydrogen, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted aromatic group, or an unsubstituted or substituted aromatic heterocyclic group and may join to complete a condensed ring, along with other types of aromatic methylidene compounds wherein the moieties attached to the naphthalene ring are attached to different positions of the ring. The preparation of the methylidene compounds is also described along with intermediate compounds and their preparation.Type: GrantFiled: January 24, 2002Date of Patent: October 7, 2003Assignee: Matsushita Electric Industrial Co., Ltd.Inventor: Mitsuru Hashimoto
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Publication number: 20030146420Abstract: Organic dye molecular materials prepared by coupling existing organic chromophore molecules to benzene or carbazole derivatives and nonlinear optical polymeric compounds having polyimide repeating units coupled with the organic dye molecular material are provided.Type: ApplicationFiled: February 27, 2002Publication date: August 7, 2003Inventors: Jung Yun Do, Myung Hyun Lee, Seung Koo Park, Jung Jin Ju, Suntak Park
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Patent number: 6552229Abstract: Disclosed is a method for preparing a 4-nitroso-substituted aromatic amine that includes contacting an amide compound with a nitroaromatic compound in the presence of a base and a solvent to directly prepare 4-nitroso-substituted aromatic amine as a main product and 4-nitro-substituted aromatic amine as a by-product without producing 4-nitroso- or 4-nitro-substituted amide as an intermediate.Type: GrantFiled: July 31, 2002Date of Patent: April 22, 2003Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young-J Joo, Jin-Eok Kim, Jeong-Im Won
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Patent number: 6521794Abstract: For the production of an aromatic compound by hydrolyzing and decarboxylating a corresponding aromatic cyano compound in the presence of an acidic substance, this invention provides a method for the production of the aromaic compound, characterized by carrying out the reactions of hydrolysis and decarboxylaion in multiple steps. Particularly when the aromatic cyano compound contains a halogen, this method effectively prevents the reaction vessels from being corroded by the by-produced hydrogen halogenide and enables the target compound to be produced in a high yield.Type: GrantFiled: February 1, 2002Date of Patent: February 18, 2003Assignee: Nippon Shokubai Co., Ltd.Inventor: Kouichi Hirota
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Publication number: 20030008907Abstract: This invention provides a process for the preparation of a benzimidazole derivative (I) or a pharmaceutically acceptable salt thereof, 1Type: ApplicationFiled: December 19, 2001Publication date: January 9, 2003Applicant: SANKYO COMPANY, LIMITEDInventors: Naoyuki Kishi, Yoshitaka Nakamura, Narumi Abe, Toyonori Takebayashi
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Patent number: 6310253Abstract: A method is disclosed for the preparation of very small particle size, relatively pure 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). Particles of TATB prepared according to the disclosed method are of submicron size and have a surface area in the range from about 3.8 to 27 square meters per gram.Type: GrantFiled: May 22, 1985Date of Patent: October 30, 2001Assignee: The United States of America as represented by the Department of EnergyInventors: Lester P. Rigdon, Gordon L. Moody, Raymond R. McGuire
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Patent number: 6262277Abstract: Provided are novel benzothiepines, derivatives, and analogs thereof; pharmaceutical compositions containing them; and methods of using these compounds and compositions in medicine, particularly in the prophylaxis and treatment of hyperlipidemic conditions such as those associated with atherosclerosis or hypercholesterolemia, in mammals.Type: GrantFiled: November 19, 1999Date of Patent: July 17, 2001Assignee: G.D. Searle and CompanyInventors: Len F. Lee, Shyamal C. Banerjee, Horng-Chih Huang, Jinglin J. Li, Raymond E. Miller, David B. Reitz, Samuel J. Tremont
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Patent number: 6242657Abstract: In the reaction of aromatic compounds with nitrating acids comprising HNO3 and, if appropriate, H2SO4 and/or H2O and/or H3PO4 to form aromatic nitro compounds, according to the invention an amount of from 0.5 to 20,000 ppm of one or more surface-active substances from the group of the anionic, cationic, zwitterionic or nonionic surface-active substances is added to the reaction mixture.Type: GrantFiled: April 26, 2000Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
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Patent number: 6225503Abstract: A method is disclosed for the preparation of very small particle size, relatively pure 1,3,5-triamino-2,4,6-trinitrobenzene (TATB). Particles of TATB prepared according to the disclosed method are of submicron size and have a surface area in the range from about 3.8 to 27 square meters per gram.Type: GrantFiled: April 3, 1992Date of Patent: May 1, 2001Assignee: The United States of America as represented by the United States Department of Energy.Inventors: Lester P. Rigdon, Gordon L. Moody, Raymond R. McGuire
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Patent number: 6169206Abstract: 4-(N,N-Dialkylamino)aniline compounds of the following general formula (I): wherein R1 represents an alkyl group, an aryl group or a heterocyclic group, R2 to R5 each represent a hydrogen atom or a substituent, and R2 and R3, R1 and R2, or R4 and R5 may form a ring together; a processing composition for color photography, which contains at least one of these compounds; and a color image-forming method wherein at least one of these aniline compounds is used.Type: GrantFiled: January 24, 2000Date of Patent: January 2, 2001Assignee: Fuji Photo Film Co., Ltd.Inventors: Keizo Kimura, Shigeo Hirano, Hiroshi Kawamoto
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Patent number: 6143208Abstract: An optical frequency conversion element has a wave-guiding layer which consists of a .chi..sup.(2) -active ferroelectric liquid crystal. The monomeric or polymeric liquid crystal material has a periodic structure which permits the so-called quasi phase matching of a guided laser beam. The period length of the structure is equal to twice the coherence length l.sub.c =.pi./.DELTA..beta. of the material, whereby .DELTA..beta.=.beta..sub.o (2.omega.)-2.beta..sub.o (.omega.), with .omega.=angular frequency of the fundamental wave, 0=zero-order mode and .beta.=propagation constant of the mode.Type: GrantFiled: February 12, 1997Date of Patent: November 7, 2000Assignee: Rolic AGInventors: Richard Buchecker, Xin Hua Chen, Jurg Fufschilling, Rolf-Peter Herr, Martin Schadt, Klaus Schmitt
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Patent number: 6069277Abstract: The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).Type: GrantFiled: November 12, 1997Date of Patent: May 30, 2000Assignee: The Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
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Patent number: 6018079Abstract: A simple and inexpensive process is described for reducing the concentration of N-nitroso-containing compounds in compositions comprising N-nitroso-containing compounds and other desired compounds wherein the N-nitroso-containing compounds thermally decompose at a temperature below the decomposition temperature of the desired compounds. For compositions comprising dinitroaniline herbicides wherein the N-nitroso compound is a N-nitroso derivative of a precursor in the manufacture of the herbicide, for example Flumetralin, N-ethyl-N-(2-chloro-6-fluorobenzyl)-2,6-dinitro-4-trifluoromethylaniline, the process requires heating the mixture to a temperature greater than about 120.degree. C., and holding the composition at that temperature for a time effective to decompose the N-nitroso compound present in the mixture. Volatile decomposition products are advantageously removed from the composition.Type: GrantFiled: May 10, 1999Date of Patent: January 25, 2000Assignee: SRM Chemical, Ltd, Co.Inventors: Lowell J. Lawrence, Stephan Kwiatkowski
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Patent number: 5959149Abstract: A method for the purification of dinitroanilines having herbicidal activity by means of the known reactions of denitrosation using acid, and denitration in a neutral or basic environment in the presence of a phase-transfer catalyst, wherein:the denitrosation reaction is effected on the dinitration mixture containing the dinitroaniline of interest and the corresponding unwanted N-nitroso- and N-dinitroaniline impurities, and in the absence of solvent,the denitration reaction is conducted sequentially to the denitrosation reaction in the same reactor with the addition to the denitrosation product as such of an aqueous base, and of the said phase-transfer catalyst.Type: GrantFiled: July 10, 1998Date of Patent: September 28, 1999Assignee: Finchimica S.p.A.Inventor: Gianluca Bernardi
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Patent number: 5922913Abstract: Disclosed is a process of nitrating or dinitrating an aromatic amine compound that involves reacting the aromatic amine and nitric acid in the presence of acetic acid such that the molar ratio of the aromatic amine compound to acetic acid is from about 1:2 to about 1:16, and the molar ratio of nitric acid to the aromatic amine is between about 1.0 to about 1.5 times the nitric acid needed to complete the reaction. More particularly, the invention is a process of forming Pendimethalin, N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine, from N-(1-ethylpropyl)-3,4-xylidine (4-NAX) that involves reacting 4-NAX and nitric acid in the presence of acetic acid such that the molar ratio of nitric to the 4-NAX is between about 2:1 and about 3:1, preferably between about 2:1 and about 2.6:1, and such that the molar ratio of 4-NAX to acetic acid is between about 1:2 to about 1:16, preferably between about 1:4 and about 1:8.Type: GrantFiled: November 6, 1998Date of Patent: July 13, 1999Assignee: SRM Chemical, Ltd., Co.Inventors: Lowell J. Lawrence, Stefan Kwiatkowski, Paul D. Smith
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Patent number: 5910578Abstract: Azo dyes of the formula ##STR1## where X is oxygen or a radical of the formula NR.sup.6, where R.sup.6 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl,R.sup.1 is substituted or unsubstituted C.sub.1 -C.sub.13 -alkyl or substituted or unsubstituted phenyl,Y is hydrogen, halogen or cyano,Z is nitro or additionally cyano when Y is halogen or cyano,R.sup.2 is C.sub.1 -C.sub.4 -alkyl, methoxymethyl or substituted or unsubstituted phenyl,R.sup.3 is hydrogen, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkyl, andR.sup.4 and R.sup.5 are each substituted or unsubstituted C.sub.2 -C.sub.13 -alkyl or C.sub.2 -C.sub.6 -alkenyl,are useful for dyeing or printing synthetic materials and are synthesizable using novel dinitroaminoaromatics as diazo components.Type: GrantFiled: July 15, 1998Date of Patent: June 8, 1999Assignee: BASF AktiengesellschaftInventors: Peter Saling, Erhard Klahr, Helmut Reichelt, Sabine Gruettner-Merten
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Patent number: 5792221Abstract: A hydroxypropylated 2-nitro-p-phenylenediamine of formula (I), wherein R1 is a C1-4 alkyl, .beta.-hydroxyethyl, .beta.-hydroxypropyl or .gamma.-hydroxypropyl radical; R2 and R3 independently represent a .beta.-hydroxyethyl, .beta.-hydroxypropyl, .gamma.-hydroxypropyl or .beta.,.gamma.-dihydroxypropyl radical, with the proviso that at least one of R1, R2 and R3 is a .gamma.-hydroxypropyl radical, while the other two are not both a .beta.-hydroxyethyl radical; and cosmetically acceptable salts thereof. This compound may be used for directly dyeing hair to give blue through purplish blue shades which are wash-fast, light-fast, waterproof and sweat resistant.Type: GrantFiled: November 25, 1996Date of Patent: August 11, 1998Assignee: L'OrealInventors: Alain Lagrange, Alex Junino, Alain Genet, Jean Cotteret
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Patent number: 5770545Abstract: This invention relates to pendralin ?2,6-dinitro-N-(1-ethylpropyl)-4-tert-butylaniline!, preemergence and postemergence herbicidal methods and herbicidal compositions employing pendralin.Type: GrantFiled: March 14, 1997Date of Patent: June 23, 1998Assignee: SRM Chemical, Ltd. Co.Inventors: Lowell J. Lawrence, Terry L. Johnson, Stephan Kwiatkowski, Paul D. Smith
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Patent number: 5709720Abstract: Aromatic ethers of polyalkylphenoxyalkanols having the formula: ##STR1## or a fuel soluble salt thereof, wherein R is hydroxy, nitro or --(CH.sub.2).sub.x -NR.sub.5 R.sub.6, wherein R.sub.5 and R.sub.6 are independently hydrogen or lower alkyl having 1 to carbon atoms, and x is 0 or 1;R.sub.1 is hydrogen, hydroxy, nitro or --NR.sub.7 R.sub.8, wherein R.sub.7 and R.sub.8 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms;R.sub.2 and R.sub.3 are independently hydrogen or lower alkyl having 1 to 6 carbon atoms; andR.sub.4 is a polyalkyl group having an average molecular weight in the range of about 450 to 5,000.The compounds of formula I are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: November 7, 1996Date of Patent: January 20, 1998Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5685881Abstract: Aromatic allylaminonitro compounds corresponding to formula (I): ##STR1## in which R.sup.1 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, R.sup.2 is hydrogen, an alkyl group containing 1 to 4 carbon atoms or an allyl group CH.sub.2 C(R.sup.5)=CH.sub.2, where R.sup.5 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, R.sup.3 is carboxyl, hydroxy, nitro, halogen or a group NR.sup.6 R.sup.7, where R.sup.6 and R.sup.7 independently of one another represent hydrogen, an alkyl group containing 1 to 4 carbon atoms, a hydroxyalkyl or dihydroxyalkyl group containing 2 to 4 carbon atoms or an allyl group CH.sub.2 C(R.sup.8)=CH.sub.2, where R.sup.8 is hydrogen or an alkyl group containing 1 to 4 carbon atoms, and R.sup.4 is hydrogen or nitro, with the proviso that R.sup.3 and R.sup.4 are not both nitro. The compounds are useful for dyeing fibers, particularly human hair.Type: GrantFiled: June 30, 1995Date of Patent: November 11, 1997Assignee: Henkel Kommanditgesellschaft auf AktienInventors: David Rose, Horst Hoeffkes, Edgar Lieske, Iduna Matzik
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Patent number: 5683998Abstract: Novel tricyclic triazolo derivatives and pharmaceutically acceptable salts thereof, which are useful as anti-inflammation agents, anti-allergy agents or anti-PAF agents as well as processes for producing the same are disclosed. The triazolo derivatives of the present invention are represented by the formula (I): ##STR1## ?wherein R.sup.1 represents hydrogen, lower alkyl or C.sub.3 -C.sub.5 cycloalkyl; R.sup.2 and R.sup.3 respectively represent hydrogen, lower alkyl, lower alkoxy or halogen; W represents C.dbd.O or CR.sup.4 R.sup.5 (wherein R.sup.4 and R.sup.5 respectively represents hydrogen or lower alkyl); A represents C.sub.1 -C.sub.5 straight or branched saturated or unsaturated alkylene which may contain one or more hetero atoms; l represents 0 to 2, n represents 1 to 3, . . . represents single bond or double bond; Y represents N or C; Z represents C(B)Ar.sup.1 Ar.sup.2 (wherein B represents hydrogen, hydroxy or methoxy, Ar.sup.1 and Ar.sup.Type: GrantFiled: May 2, 1995Date of Patent: November 4, 1997Assignee: Toray Industries, Inc.Inventors: Katsuhiro Shibayama, Tetsuya Makino, Takayuki Imaoka, Tetsuya Katou, Masayuki Kaneko
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Patent number: 5672760Abstract: The present invention provides an ablatively photodecomposable polymer having a photoabsorber bound to the polymer (the "ablatively photodecomposable polymer") which does not phase separate, nor does it crystallize. The ablatively photodecomposable polymer provides even ablation, high resolution and in preferred embodiments, can withstand potassium permanganate etchant and ferric chloride etchant. The ablatively photodecomposable polymer is strippable, although it can remain on the substrate if desired. The ablatively photodecomposable polymer comprises a polymer to which a photoabsorber is bound, either covalently or ionically. The present invention is also directed to a process for forming a metal pattern on a substrate employing the ablatively photodecomposable polymer.Type: GrantFiled: April 9, 1996Date of Patent: September 30, 1997Assignee: International Business Machines CorporationInventors: Francis Charles Burns, William Weathers Fleming, Victor Yee-Way Lee, Randy William Snyder
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Patent number: 5663308Abstract: Organosilicon polymers, including crosslinked polymers and crosslinkable prepolymers, of cyclic polysiloxane, organic dyes, and, optionally, polyenes. The dyes include those with delocalized Pi electron systems linking electron donor groups and electron acceptor groups, and with at least two carbon-carbon double bond-containing pendant groups attached to at least two different sites from among the indicated delocalized Pi electron systems, donor groups, and acceptor groups.Type: GrantFiled: February 7, 1994Date of Patent: September 2, 1997Assignee: Hercules IncorporatedInventors: Wayne Michael Gibbons, Robert Paul Grasso, Michael Kevin O'Brien, Paul Joseph Shannon, Shao-Tang Sun
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Patent number: 5648543Abstract: Disclosed is a process for producing a 4-nitrosodiphenylamine of the formula (2) ##STR1## wherein R.sub.1 and R.sub.2 independently represent hydrogen atom, methyl group, ethyl group, cyclohexyl group, methoxy group, ethoxy group or chlorine or bromine atom, or a salt thereof, comprising treating a diphenylamine represented by the formula (1) ##STR2## wherein R.sub.1 and R.sub.2 are as defined above with (i) a mixture of nitrogen oxides, (ii) a hydrogen halide and (iii) an aliphatic alcohol, wherein the atomic ratio of oxygen to nitrogen of the mixture of nitrogen oxides is more than 1.0 and less than 2.0. This process produces 4-nitrosodiphenylamine of the formula (2) or a salt thereof conveniently and effectively, and is industrially advantageous.Type: GrantFiled: June 6, 1995Date of Patent: July 15, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Tetsuo Murata, Hiroyuki Takagi, Yasumi Katayama
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Patent number: 5637256Abstract: This invention provides chiral nonracemic compound of formula: ##STR1## wherein n and m are 0 or 1, but one of n or m must be 1; k=0 or 1; B=COO or OOC; X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are either H, an electron donor or an electron acceptor where at least one of the groups X.sub.1, X.sub.2, X.sub.3 or X.sub.4 is an electron acceptor and at least one of these groups is an electron donor and when one of X.sub.1 or X.sub.3 is an electron donor, the other is an electro a acceptor and when one of X.sub.2 or X.sub.4 is an electron donor, the other is an electron acceptor; and R.sub.1 and R.sub.2 can be various substituted and unsubstituted alkanes and monoalkenes. Compounds provided include those where one of R.sub.1 or R.sub.2 is a chiral non-racemic tail group, particularly a group selected from --O--C.sup.* H(CH.sub.3)R.sub.c, --O--C.sup.* H(CH.sub.3)COOR.sub.d, and --O--CH.sub.2 C.sup.* HF--C.sup.* HF--R.sub.2 in which the .sup.* indicates an asymmetric carbon enriched in one stereoconfiguration where R.Type: GrantFiled: May 26, 1995Date of Patent: June 10, 1997Assignee: University Research CorporationInventors: David M. Walba, Maria B. Ros, James A. Rego, Teresa Sierra
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Patent number: 5637119Abstract: Substituted aromatic polyalkyl ethers having the formula: ##STR1## wherein R.sub.1 is a polyalkyl group having an average molecular weight of about 450 to about 5,000;A is nitro, amino, cyano, aminomethyl, N-alkylamino or N-alkylaminomethyl wherein the alkyl group contains from about 1 to about 6 carbon atoms, or N,N-dialkylamino or N,N-dialkylaminomethyl wherein each alkyl group independently contains from about 1 to about 6 carbon atomsx is an integer from about 0 to about 1; and y is an integer from about 0 to about 10 with the proviso that one of x and y must be 0 and the other must be greater than 0.The substituted aromatic polyalkyl ethers of the present invention are useful as fuel additives for the prevention and control of engine deposits.Type: GrantFiled: December 29, 1995Date of Patent: June 10, 1997Assignee: Chevron Chemical CompanyInventor: Richard E. Cherpeck
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Patent number: 5633407Abstract: 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: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5618979Abstract: 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: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5616810Abstract: The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula ( I ) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which:R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups;R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG);R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect;with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect.A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation.Type: GrantFiled: March 28, 1995Date of Patent: April 1, 1997Assignee: Rhone-Poulenc ChimieInventor: Jean-Marc Ricca
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Patent number: 5597922Abstract: Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia and surgery, as well as treating neurodegenerative diseases including Alzheimer's disease, amyotrophic lateral sclerosis, Huntington's disease and Down's syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions and inducing anesthesia are disclosed by administering to an animal in need of such treatment a compound which has high binding to the glycine receptor.Type: GrantFiled: July 29, 1994Date of Patent: January 28, 1997Assignees: State of Oregon, Acting by and through the Oregon State Board of Higher Education, Acting for and on Behalf of the Oregon Health Sciences University and the University of Oregon, Acea Pharmaceuticals, Inc., The Regents of the University of CaliforniaInventors: Sui X. Cai, John F. W. Keana, Eckard Weber
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Patent number: 5596100Abstract: A method is provided for the regioselective, palladium catalyzed carbo- or heteroannulation of internal alkynes by aryl iodides containing o-substituted side chains to yield aromatic carbocyclic and heterocyclic ring systems.Type: GrantFiled: April 4, 1995Date of Patent: January 21, 1997Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 5585522Abstract: Novel amino substituted bishalomethyl benzene compounds, which are precurs to phenylene polymers are disclosed having non-linear optical properties, and which can be converted to electrically conductive polymers. Such polymers are produced by reacting a novel amino substituted bishalomethyl benzene compound with a dialkyl sulfide to make a bis-cycloalkylene sulfonium salt of 2,5,N,N-tetramethylaniline hydrochloride, which is 2,5-(N,N-dimethyl)aniline hydrochloride dimethylene bis-(tetramethylene sulfonium chloride) and reacting this sulfonium salt with alkali metal hydroxide to form a cycloalkylene sulfonium salt precursor polymer, and then heating the precursor polymer under conditions to produce the amino substituted phenylene vinylene polymer, such as poly(2-(N,N-dimethylamino) phenylene vinylene). The polymers can also be made directly by treatment of the bis chlormethyl dimethyl aminobenzene hydrochloride derivative with alkali metal alkoxide.Type: GrantFiled: May 10, 1995Date of Patent: December 17, 1996Assignee: The United States of America as represented by the Secretary of the NavyInventors: John D. Stenger-Smith, William P. Norris, Andrew P. Chafin
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Patent number: 5569783Abstract: The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by:(a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from --H, or --NH.sub.2, with the proviso that at least 1 or 2 of X, Y, and Z are hydrogen,with an amount effective to produce DATB or TATB of 1,1,1-trialkylhydrazinium halide wherein alkyl is selected from methyl, ethyl, propyl or butyl and halide is selected from chloride, bromide or iodide.Type: GrantFiled: May 12, 1995Date of Patent: October 29, 1996Assignee: The Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
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Patent number: 5516942Abstract: A N1,N4-dihydroxyethylated 2-nitro-p-phenylenediamine of formula (I), wherein R is C3-4 aklyl, and cosmetically acceptable salts thereof, for use in direct dyeing to give blue through purple shades which are wash-fast, light-fast, weatherproof and sweat resistant, and optionally combined with yellow and optionally read or orange-coloured dyes to give natural hues.Type: GrantFiled: December 7, 1994Date of Patent: May 14, 1996Assignee: L'OrealInventors: Alain Lagrange, Alex Junino, Alain Genet, Jean Cotteret
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Patent number: 5510534Abstract: The present invention is directed to a process for reducing the nitrosamine content in a herbicide derived from dinitroaniline. The herbicide is treated with an aqueous solution of alkaline or ammonium persulfate in a proportion of at least 0.5% w/w relative to the weight of the herbicide to form an aqueous suspension. The suspension is heated to at least 70.degree. C., and the herbicide is separated from the suspension.Type: GrantFiled: March 23, 1995Date of Patent: April 23, 1996Assignee: Atanor S.A.Inventors: Maria D. C. Breglia De Belcoure, Marta M. D. C. Ruiz
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Patent number: 5508467Abstract: The present invention relates to a process for the preparation of compounds of the general formula I ##STR1## by reaction of compounds of the general formula II ##STR2## with compounds of the general formula III ##STR3## in inert aprotic solvents in the presence of a base and subsequent rearrangement of the resulting intermediate compound with an alkali metal hydroxide, characterized in that the intermediate compound is not isolated.Type: GrantFiled: August 22, 1994Date of Patent: April 16, 1996Assignee: Cassella AktiengesellschaftInventors: Wolfgang Bauer, Klaus Delpy, Andreas Bittner
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Patent number: 5466871Abstract: A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.Type: GrantFiled: July 11, 1994Date of Patent: November 14, 1995Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5446186Abstract: The synthesis and compound of a new caged calcium which is an ortho-nitrophenyl derivative of EGTA and various intermediates. It is synthesized in ten steps and 24% overall yield. The photosensitive chelator, nitrophenyl-EGTA, has a K.sub.d for Ca.sup.2+ of 80 nM and for Mg.sup.2+ of 8.8 mM. Upon exposure to ultra-violet light (in the region of 350 nm), the chelator is cleaved, yielding iminodiacetic acid photoproducts with known low Ca-affinity (K.sub.d =1 mM). The quantum yield of photolysis of nitrophenyl-EGTA in the presence of Ca.sup.a+ is 0.23 and in the absence of Ca.sup.2+ is 0.20. In experiments with chemically skinned skeletal muscle fibers, a fully relaxed fiber equilibrated with nitrophenyl-EGTA:Ca.sup.2+ complex, in the presence of physiological [Mg.sup.2+ ] (i.e. 1.0 mM), produced maximal contraction after a single flash from a frequency doubled ruby laser (347 nm). Half-maximal tension was achieved in 18 ms at 15.degree. C.Type: GrantFiled: November 9, 1993Date of Patent: August 29, 1995Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
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Patent number: 5436372Abstract: The invention is intended to provide novel solid state displacement elements that have an extent of displacement. The solid state displacement element has an intercalation compound in which a polar compound (B) is mixed with an inorganic layered compound (A), and produces a strain when a voltage is applied.Type: GrantFiled: April 9, 1992Date of Patent: July 25, 1995Assignee: Nippon Soken, Inc.Inventors: Hiroyuki Yoshida, Eturo Yasuda, Yoshiaki Fukushima
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Patent number: 5414125Abstract: A diamino-alpha-alkylstilbene useful as an epoxy resin curing agent is represented by the following Formula I: ##STR1## wherein R is independently hydrogen, a C.sub.1 -C.sub.10 hydrocarbyl(oxy) group or a halogen, nitro, nitrile, phenyl or --CO--R.sup.1 group wherein R.sup.1 is independently hydrogen or a C.sub.1 -C.sub.3 hydrocarbyl group; each R.sup.4 is independently hydrogen or a C.sub.1 -C.sub.10 hydrocarbyl group; and Y is a ##STR2## group wherein n=0 or 1.Type: GrantFiled: July 23, 1993Date of Patent: May 9, 1995Assignee: The Dow Chemical CompanyInventors: Robert E. Hefner, Jr., Jimmy D. Earls