Nitro Or Nitroso Patents (Class 562/434)
  • Patent number: 6271416
    Abstract: The present invention relates to a simple method for preparing a quinolinone derivative, which is effective as a medicine, e.g., as an agent for treating allergic diseases and the like; novel amide derivatives effective as an intermediate in the method, novel quinolinone derivatives obtained according to the method; and an anti-allergic agent containing a quinolinone derivative and/or physiological salt of the same as the active ingredients.
    Type: Grant
    Filed: June 20, 2000
    Date of Patent: August 7, 2001
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Hidetsugu Takagaki, Shinobu Yamaguchi, Masayoshi Abe, Mitsuru Sakai, Osamu Misumi
  • Publication number: 20010005762
    Abstract: The present invention provides a method of producing easily and in a high yield a threo-2-hydroxy-3-nitrobutanoic acid compound or a mixture of a threo- and an erythro-2-hydroxy-3-nitrobutanoic acid compounds, this mixture having an erythro compound:threo compound ratio of about 1:1, which method includes reacting, in a solvent, a 2-hydroxy-3-nitrobutanoic acid compound having the formula (I) 1
    Type: Application
    Filed: December 27, 2000
    Publication date: June 28, 2001
    Inventors: Tetsuya Shintaku, Masahide Tanaka, Nobushige Itaya
  • Patent number: 6177463
    Abstract: The invention relates to new oxime derivatives, to a plurality of processes for their preparation, and to their use as pesticides.
    Type: Grant
    Filed: September 3, 1996
    Date of Patent: January 23, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Peter Gerdes, Herbert Gayer, Bernd-Wieland Kr{umlaut over (u)}ger, Bernd Gallenkamp, Heinz-Wilhelm Dehne, Stefan Dutzmann, Gerd H{umlaut over (a)}nssler, Klaus Stenzel
  • Patent number: 6162943
    Abstract: Process for the preparation of .alpha.-alkoxy-.alpha.-trifluoromethyl-arylacetic esters of the formula (I) ##STR1## wherein R is a component selected from the group consisting of C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.6 -C.sub.10 -aryl and C.sub.1 -C.sub.6 -halogenoalkyl, R' is selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, X is selected from the group consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.6 -C.sub.10 -aryl or C.sub.1 -C.sub.4 -alkoxy and nitro, and n is zero or an integer from 1 to 3.
    Type: Grant
    Filed: April 16, 1999
    Date of Patent: December 19, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Albrecht Marhold
  • Patent number: 6147224
    Abstract: Compounds of Formula 1, Formula 2 or Formula 3 where X is O, S, or (CR.sub.1 R.sub.1).sub.n where n is 0, 1 or 2; Y is a bivalent radical having Formula 4 or Formula 5 where o is an integer from 1 to 4 ##STR1## or Y is a bivalent aryl or 5 or 6 membered heteroaryl radical having 1 to 3 heteroatoms selected from N, S and O, said aryl or heteroaryl groups being unsubstituted, or substituted with 1 to 3 C.sub.1-6 alkyl or with 1 to 3 C.sub.1-6 fluoroalkyl groups; and the remaining symbols have the meaning described in the specification, have RXR selective retinoid agonist-like activity.
    Type: Grant
    Filed: October 1, 1998
    Date of Patent: November 14, 2000
    Assignee: Allergan Sales, Inc.
    Inventors: Vidyasagar Vuligonda, Kwok Yin Tsang, Jayasree Vasudevan, Roshantha A. Chandraratna
  • Patent number: 6054609
    Abstract: A method of separating 3-nitro-o-toluic acid and 5-nitro-o-toluic acid from a mixture of said isomers, comprising producing salts by adding an aromatic organic base, for example, aniline or pyridine, to the said mixture, separating said salts into solids and a mother liquor, by taking advantage of the difference in solubilities between the said salts to water or a mixed solvent consisting of water and a water-soluble organic compound, for example, methanol, and, further, recovering 3-nitro-o-toluic acid from the mother liquor and 5-nitro-o-toluic acid from the solids.
    Type: Grant
    Filed: November 19, 1998
    Date of Patent: April 25, 2000
    Assignee: Sumikin Chemical Co., Ltd.
    Inventors: Keiichi Yokota, Ikuo Ito, Seiji Takeuchi
  • Patent number: 6048896
    Abstract: 4-Phenyl-4-oxo-butenoic acid derivatives for use in the treatment of the human or animal body by therapy; particularly as kynurenine-3-hydroxylase inhibitors, in the prevention and/or treatment of a neurodegenerative disease wherein the inhibition of such an enzyme is needed. The present invention further comprises a selected class of the above mentioned 4-phenyl-4-oxo-butenoic acid derivatives, their pharmaceutically acceptable salts, a process for their preparation and pharmaceutical compositions containing them.
    Type: Grant
    Filed: May 4, 1998
    Date of Patent: April 11, 2000
    Assignee: Pharmacia & Upjohn S.p.A.
    Inventors: Antonio Giordani, Paolo Pevarello, Carmela Speciale, Mario Varasi
  • Patent number: 6028219
    Abstract: A process for the preparation of a compound of general formula I: ##STR1## wherein: R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl, any of which may optionally be substituted with one or more substituents selected from halogen and OH; or COOR.sup.4, COR.sup.6, CONR.sup.4 R.sup.5 or CONHSO.sub.2 R.sup.4 ;R.sup.4 and R.sup.5 are each independently hydrogen or C.sub.1 -C.sub.4 alkyl optionally substituted with one or more halogen atoms;R.sup.6 is a halogen atom or a group R.sup.4 ;R.sup.2 is hydrogen or halo;R.sup.3 is C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl or C.sub.2 -C.sub.4 alkynyl, any of which may optionally be substituted with one or more halogen atoms; or halo;the process comprising reacting a compound of general formula II: ##STR2## wherein R.sup.1, R.sup.2 and R.sup.
    Type: Grant
    Filed: July 28, 1997
    Date of Patent: February 22, 2000
    Assignee: Zeneca Limited
    Inventors: John Heathcote Atherton, Stephen Martin Brown, James Peter Muxworthy, Martin Lennon
  • Patent number: 5998661
    Abstract: A process for selective, direct oxidation of amine or amine hydrochloride mpounds is described. It uses mixed oxidizing agents of monopersulfate and ozone.
    Type: Grant
    Filed: June 15, 1998
    Date of Patent: December 7, 1999
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventor: Abdollah Bashir-Hashemi
  • Patent number: 5990165
    Abstract: A pharmaceutical compound of the formula: ##STR1## in which n is 1 or 2, R.sup.1 is --CO.sub.2 H, R.sup.2 is hydrogen or C.sub.1-4 alkyl andR.sup.3 is hydrogen, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, optionally substituted phenyl, optionally substituted phenyl-C.sub.1-4 alkyl, optionally substituted phenyl C.sub.2-10 alkenyl,(optionally substituted phenyl).sub.2 -C.sub.1-4 alkyl, optionally substituted C.sub.3-7 cycloalkyl, optionally substituted C.sub.3-7 cycloalkyl-C.sub.1-4 alkyl or optionally substituted C.sub.3-7 cycloalkyl-C.sub.2-10 alkenyl, orR.sup.2 and R.sup.3, together with the carbon atom to which they are attached, form an optionally substituted C.sub.4-7 cycloalkyl group;or a salt or ester thereof other than the compounds .gamma.-propylidene-L-glutamic acid, .gamma.-ethylidene-L-glutamic acid and .gamma.-methylidene-L-glutamic acid.
    Type: Grant
    Filed: March 24, 1998
    Date of Patent: November 23, 1999
    Assignee: Lilly, S.A.
    Inventors: Concepcion Pedregal Tercero, Almudena Rubio Esteban
  • Patent number: 5955505
    Abstract: A method comprising administering a sulfonamide derivative to a patient requiring activation of glutamate receptors, the sulfonamide derivative represented by the formula ##STR1## wherein A is a napthyl group, a pyridyl group, a phenyl group, a phenyl group substituted by 1 to 5 members selected from the group consisting of a halogen atom, an alkyl group having 1 to 40 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, and an acetamido group, or an alkyl group having 1 to 20 carbon atoms; B is an alkylene group having 1 to 3 carbon atoms, a group of --OCH.sub.2 -- or a group of --CH.dbd.CH--; X and Y are the same or different, and are each a hydrogen atom or a fluorine atom; R is a carboxy group, an alkoxycarbonyl group having 2 to 5 carbon atoms, a hydroxymethyl group or a group of ##STR2## wherein R.sub.1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; and R.sub.
    Type: Grant
    Filed: August 20, 1997
    Date of Patent: September 21, 1999
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Jiro Takeo, Shinya Yamashita, Keiji Wada, Yoshiyuki Chiba
  • Patent number: 5952531
    Abstract: A process for the nitration of an aromatic or heteroaromatic compound with a nitrating agent comprising nitric acid or a mixture of nitric and sulphuric acids, characterised in that nitration is performed in a solvent comprising at least 50% v/v of a C.sub.1 -C.sub.6 alkyl ester of a C.sub.1 -C.sub.4 carboxylic acid. The process is of particular use for the nitration of diphenyl ethers to give compounds which are useful as herbicides or as intermediates in the synthesis of herbicides.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: September 14, 1999
    Assignee: Zeneca Limited
    Inventors: Ian Jeffrey Grassham Priestley, James Peter Muxworthy, John Heathcote Atherton, Martin Lennon, Stephen Martin Brown
  • Patent number: 5932763
    Abstract: The present invention provides pharmaceutical compositions and methods for treating certain conditions comprising administering an amount of a compound or composition of the invention which is effective to inhibit the activity of at least one matrix metalloprotease, resulting in achievement of the desired effect. The compounds of the present invention are of the generalized formula ##STR1## where v is 1, 2, 3 or 4 and Ar represents a substituted aromatic moiety.
    Type: Grant
    Filed: May 15, 1997
    Date of Patent: August 3, 1999
    Assignee: Bayer Corporation
    Inventors: William J. Scott, Margaret A. Popp, David S. Hartsough
  • Patent number: 5932616
    Abstract: The present invention provides the compound having the structure: ##STR1## wherein each of R.sub.1 and R.sub.2 are independently the same as or different from each other; when R.sub.1 and R.sub.2 are the same, each is a substituted or unsubstituted arylamino, cycloalkylamino, pyridineamino, piperidino, 9-purine-6-amine, or thiozoleamino group; when R.sub.1 and R.sub.2 are different, R.sub.1 =R.sub.3 --N--R.sub.4, wherein each of R.sub.3 and R.sub.4 are independently the same as or different from each other and are a hydrogen atom, a hydroxyl group, a substituted or unsubstituted, branched or unbranched alkyl, alkenyl, cycloalkyl, aryl, alkyloxy, aryloxy, arylalkyloxy, or pyridine group, or R.sub.3 and R.sub.4 bond together to form a piperidine group and R.sub.2 is a hydroxylamino, hydroxyl, amino, alkylamino, dialkylamino or alkyloxy group; and n is an integer from about 4 to about 8.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: August 3, 1999
    Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia Univerisity in the City of New York
    Inventors: Ronald Breslow, Paul A. Marks, Richard A. Rifkind, Branko Jursic
  • Patent number: 5929117
    Abstract: Cyano and carboxy derivatives of substituted styrenes are inhibitors of tumor necrosis factor .alpha., nuclear factor .kappa.B, and phosphodiesterase and can be used to combat cachexia, endotoxic shock, retrovirus replication, asthma, and inflammatory conditions. A typical embodiment is 3,3-bis-(3,4-dimethoxyphenyl)acrylonitrile.
    Type: Grant
    Filed: August 11, 1997
    Date of Patent: July 27, 1999
    Assignee: Celgene Corporation
    Inventors: George W. Muller, Mary Shire
  • Patent number: 5869734
    Abstract: A process for preparing optically active (S)-(-) and (R)-(+)-deoxyspergualin and salts thereof of the formula I ##STR1## by reacting a compound of formula II ##STR2## with a compound of formula III ##STR3## in the presence of a condensing/dehydrating agent and an organic or inorganic base in an organic solvent to form a compound of formula IV ##STR4## which can then be converted to the desired final product of formula I via deprotection and hydrogenolysis.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: February 9, 1999
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Xuebao Wang, John K. Thottathil
  • Patent number: 5808003
    Abstract: A compound according to the formula: ##STR1## and conjugates thereof.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: September 15, 1998
    Assignee: PerImmune Holdings, Inc.
    Inventors: Ramaswamy Subramanian, James Colony
  • Patent number: 5731454
    Abstract: A family of compounds has been found to be useful for right-shifting hemoglobin towards a low oxygen affinity state. The compounds are capable of acting on hemoglobin in whole blood. In addition, the compounds can maintain the oxygen affinity in blood during storage and can restore the oxygen affinity of outdated blood.
    Type: Grant
    Filed: January 18, 1995
    Date of Patent: March 24, 1998
    Assignee: Virginia Commonwealth University
    Inventors: Donald J. Abraham, Gajanan Joshi, Ramnarayan Randad, Jayashree Panikker
  • Patent number: 5721234
    Abstract: Novel glutamate receptor antagonists represented by the formula ##STR1## or a pharmaceutically acceptable salt thereof, whereinZ is an alicyclic fused ring having 5 to 7 carbon atoms;R.sup.1 is hydrogen, an alkyl or an arylalkyl; andA is O, CH.sub.2, NR.sup.4, CH.sub.2 NR.sup.4, CN, tetrazole or CO wherein R.sup.4 is hydrogen, alkyl, hydroxyalkyl, aminoalkyl or aralkyl, wherein(i) when A is O, CH.sub.2, NR.sup.4 or CH.sub.2 NR.sup.4 then B is hydrogen, alkyl, alkenyl, alkynyl, aryl, aralkyl, hydroxyalkyl, alkoxy, aminoalkyl, heterocyclic, alkylheterocyclic, heterocyclic-methyl, heterocyclic-ethyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, aralkylcarbonyl, heterocyclic-carbonyl, alkylheterocyclic-carbonyl, or when A is NR.sup.4 or CH.sub.2 NR.sup.4 then B is a naturally occurring .alpha.-amino acid moiety joined by an amide bond or B joins with R.sup.4 and the nitrogen to form a four to seven membered heterocyclic ring, provided that when Z is a fused cyclohexyl ring and R.sup.
    Type: Grant
    Filed: October 23, 1995
    Date of Patent: February 24, 1998
    Assignee: Warner-Lambert Company
    Inventors: Christopher Franklin Bigge, Daniel Martin Retz
  • Patent number: 5719317
    Abstract: A method for preparing a compound of formula (I), wherein R.sub.1 and R.sub.2, which are the same or different, are a hydrogen atom or an alkyl or alkoxy radical, or R.sub.1 and R.sub.2, taken together with the carbon atom to which they are attached, form a cycloalkyl radical containing 3-6 carbon atoms. The method comprises dehalogenating a derivative of formula (lI), wherein R.sub.1 and R.sub.2 have the same meanings as in formula (1) and Hal is a chlorine or bromine atom, using 1-2 mol of triethylammonium formate, in the presence of 0.002-0.1 mol of coal-borne palladium per mol of the compound of formula (II), in aceonitrile or tetrahydrofuran and at a temperature between 50.degree. C. and the boiling point of the reaction medium.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: February 17, 1998
    Assignee: Rhone-Poulenc Rorer S.A.
    Inventor: Franco Manfre
  • Patent number: 5719306
    Abstract: The present invention provides compounds of the formula Ar.sup.1 --Q--Ar.sup.2 --Y--R--Z and pharmaceutically acceptable salts thereof wherein Ar.sup.1 and Ar.sup.2 are optionally substituted aryl moieties, Z is an optionally substituted nitrogen-containing moiety which may be an acyclic, cyclic or bicyclic amine or an optionally substituted monocyclic or bicyclic nitrogen-containing heteroaromatic moiety; Q is a linking group capable of linking two aryl groups; R is an alkylene moiety; Y is a linking moiety capable of linking an aryl group to an alkylene moiety and wherein Z is bonded to R through a nitrogen atom. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of inflammatory diseases which are mediated by LTB.sub.4 production, such as psoriasis, ulcerative colitis, IBD and asthma.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 17, 1998
    Assignee: G.D. Searle & Co.
    Inventors: Nizal Samuel Chandrakumar, Barbara Baosheng Chen, Michael Clare, Bipinchandra Nanubhai Desai, Stevan Wakefield Djuric, Stephen Hermann Docter, Alan Frank Gasiecki, Richard Arthur Haack, Chi-Dean Liang, Julie Marion Miyashiro, Thomas Dale Penning, Mark Andrew Russell, Stella Siu-tzyy Yu
  • Patent number: 5698738
    Abstract: Nitric oxide has proved to mediate many important physiological processes. The nitric oxide donors of the present invention have a NONOate anion linked to an ortho-substituted aryl, a heteroaromatic substituent, asteroid, or a catecholamine. Preferred ortho substituents are alkoxy, halo, and alkyl. The cation of the salt is an alkali metal, an alkaline-earth metal, an ammonium or substituted ammonium group. Nitric oxide donors provided herein are more stable than that of nitrogen-bonded NONOates described previously. The by product left after release of NO, and the nitric oxide donors themselves, are very probably less carcinogenic than the corresponding nitrogen-bonded NONOates.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: December 16, 1997
    Assignees: Board of Regents, The University of Texas System, The Texas A&M University System
    Inventors: Robert E. Garfield, Alexandru T. Balaban, William A. Seitz, Douglas J. Klein, Melanie Lesko
  • Patent number: 5688945
    Abstract: The present invention relates to novel derivatives of 3-hydroxyanthranilic acid, 3-HANA, of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and selected from H and alkyl; X is selected from alkylthio, arylthio, aryloxy, halogen and cyano; R.sup.3, R.sup.4 are the same or different and selected from halogen, methyl, fluoroalkyl, cyano and Z--R.sup.5 wherein Z is selected from CH.sub.n, NH.sub.m, O, S, SO.sub.2 and CO wherein n=1 or 2; m=0 or 1 and R.sup.5 is selected from alkyl, aryl and fluoroalkyl; or R.sup.3 and R.sup.4 together form a saturated or unsaturated ring system Y--V--Z wherein Y and Z, independently of each other, are as defined for Z above and V is selected from C.sub.1 -C.sub.3 alkylene or alkenylene, --N.dbd., --N.dbd.N-- and ##STR2## wherein R.sub.
    Type: Grant
    Filed: December 20, 1996
    Date of Patent: November 18, 1997
    Assignees: Astra Aktiebolag, The University of Maryland at Baltimore
    Inventors: Susanna Karin Maria Bjork, Birgitta Kristina Gotthammar, Mats Torbjorn Linderberg, Johan Per Luthman, Kerstin Margareta Irma Persson, Robert Schwarcz
  • Patent number: 5635608
    Abstract: The invention relates to caged compounds for the study of biological processes, where the caged compound has a photoremoveable .alpha.-carboxy-substituted o-nitrobenzyl group. Covalent attachment of the substituted o-nitrobenzyl to a parent compound yields a caged compound with biological and/or physical properties that are significantly altered from the original properties of the parent compound. Illumination of the caged compounds to cleave the photoremoveable group yields the parent compound with its original properties restored.
    Type: Grant
    Filed: November 8, 1994
    Date of Patent: June 3, 1997
    Assignee: Molecular Probes, Inc.
    Inventors: Richard P. Haugland, Kyle R. Gee
  • Patent number: 5610190
    Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV Protease.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 11, 1997
    Assignee: G. D. Searle & Co.
    Inventors: John J. Talley, Daniel P. Getman, Gary A. DeCrescenzo, Ko-Chung Lin, Michael L. Vazquez, Richard A. Mueller, Kathryn L. Reed, Robert M. Heintz, Michael Clare, John N. Freskos, Eric T. Sun
  • Patent number: 5599814
    Abstract: The present invention relates to pyridazino[4,5-b]quinolines, and pharmaceutically useful salts thereof, which are excitatory amino acid antagonists and which are useful when such antagonism is desired such as in the treatment of neurological disorders. The invention further provides pharmaceutical compositions containing pyridazino[4,5-b]quinolines as active ingredient, and methods for the treatment of neurological disorders.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Thomas M. Bare, Richard B. Sparks
  • Patent number: 5523475
    Abstract: The present invention relates to novel derivatives of 3-hydroxyanthranilic acid, 3-HANA, of the general formula I ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and selected from H, alkyl, aryl and arylalkyl; X and Y are the same or different and selected from alkoxy, aryloxy, alkyl, alkylthio, arylthio, fluoroalkyl, halogen, cyano, OSO.sub.2 CH.sub.3, OSO.sub.2 CF.sub.3, OCF.sub.3 and SCF.sub.3 with the proviso that the compound of formula I wherein R.sup.1 and R.sup.2 =H, X=Br and Y=Me is excluded;or a pharmaceutically acceptable salt thereof, methods and intermediates for their preparation, novel pharmaceutical compositions and the use thereof for inhibiting the enzyme 3-hydroxyanthranilate oxygenase, 3-HAO, responsible for the production of the endogenous neurotoxin quinolinic acid, QUIN.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: June 4, 1996
    Assignees: Aktiebolaget Astra, Cornell Research Foundation, Inc., The University of Maryland at Baltimore
    Inventors: Susanna K. M. Bjork, Barry K. Carpenter, Birgitta K. Gotthammar, Mats T. Linderberg, Johan P. Luthman, Kerstin M. I. Persson, Robert Schwarcz
  • Patent number: 5514683
    Abstract: The compounds of the formula I ##STR1## and their pharmaceutical acceptable salts, which are defined herein, are ligands for cholecystokinin and/or gastrin receptors.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: May 7, 1996
    Assignee: James Black Foundation Limited
    Inventors: Sarkis B. Kalindjian, Caroline M. R. Low, Iain M. McDonald, Robert A. D. Hull, Nigel P. Shankley, Ildiko M. Buck, Katherine I. M. Steel, Jonathan M. R. Davies, David J. Dunstone, Elaine A. Harper, Michael J. Pether, Michael J. Bodkin, Matthew J. Tozer, Martin L. Hudson
  • Patent number: 5449809
    Abstract: Acetylene derivatives of the general formula I ##STR1## where U, V and W are hydrogen, halogen, nitro, cyano, alkyl or alkoxy,A is alkylidene, alkoxymethylidene, alkylthiomethylidene or alkoximino,B is OH, alkoxy or alkylamino andR is hydrogen, halogen, cyano, CF.sub.3, alkyl, cycloalkyl, haloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, hetaryl, arylalkyl, arylalkenyl, arylethynyl, hetaryl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, aryloxyalkyl, hetaryloxyalkyl, arylamino-alkyl, arylthiomethyl, hetarylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, SiR.sup.12 R.sup.13 R.sup.14, SnR.sup.15 R.sup.16 R.sup.17, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 andR.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are hydrogen, alkyl, aryl, hetaryl, arylalkyl or hetarylalkyl and R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or aryl-C.sub.1 -C.sub.4 -alkoxy, and fungicides containing these compounds.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: September 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Wingert, Beate Hellendahl, Reinhard Kirstgen, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
  • Patent number: 5446186
    Abstract: 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: Grant
    Filed: November 9, 1993
    Date of Patent: August 29, 1995
    Inventors: Graham C. R. Ellis-Davies, Jack H. Kaplan
  • Patent number: 5442106
    Abstract: Described are preferred processes for hydrolyzing activated esters using, as catalysts, siloxanes having 4-dialkylaminopyridyl groups incorporated into their polymer backbones. The preferred siloxane catalyst materials demonstrate unexpected catalytic efficacy in the hydrolysis as well as enzyme-like selectivity for ester substrates.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: August 15, 1995
    Assignee: Indiana University Foundation
    Inventors: Martel Zeldin, Wilmer K. Fife, Slawomir Rubinsztajn
  • Patent number: 5436372
    Abstract: 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: Grant
    Filed: April 9, 1992
    Date of Patent: July 25, 1995
    Assignee: Nippon Soken, Inc.
    Inventors: Hiroyuki Yoshida, Eturo Yasuda, Yoshiaki Fukushima
  • Patent number: 5434287
    Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.
    Type: Grant
    Filed: November 4, 1993
    Date of Patent: July 18, 1995
    Assignee: The United States of America as represented by the Department of Health and Human Services
    Inventors: Otto A. Gansow, Martin W. Brechbiel
  • Patent number: 5430182
    Abstract: The present invention relates to a novel sweetening agent and to its method of preparation. This novel sweetening agent is a 2-substituted acyl derivative of L-aspartic or L-glutamic acid and has the general formula ##STR1## R being an acyl group of the formula ##STR2## and R' being a group of the formula ##STR3## R.sub.1, R.sub.2, R.sub.3, X, Y and Z being variously defined. This novel sweetening agent is essentially characterized by a high sweetening potency and a high stability compatible with the conditions of industrial use, and is applied especially for sweetening soft drinks.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: July 4, 1995
    Inventors: Claude Nofre, Jean-Marie Tinti
  • Patent number: 5414108
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: May 9, 1995
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5350872
    Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.
    Type: Grant
    Filed: October 29, 1993
    Date of Patent: September 27, 1994
    Assignee: Biogal Gyogyszergrar
    Inventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
  • Patent number: 5319122
    Abstract: This invention relates to a novel process for preparing benzylformimidates which are useful in the production of certain carbapenem antibiotics. The process of this invention provides a means of producing a high-yield, high-purity product.
    Type: Grant
    Filed: November 12, 1992
    Date of Patent: June 7, 1994
    Assignee: Merck & Co., Inc.
    Inventor: Joel J. Friedman
  • Patent number: 5288901
    Abstract: There are provided important pyrroline and glycine intermediates, methods for the preparation of said intermediates and the use thereof in the manufacture of arylpyrrole insecticidal agents.
    Type: Grant
    Filed: April 8, 1992
    Date of Patent: February 22, 1994
    Assignee: American Cyanamid Company
    Inventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
  • Patent number: 5283352
    Abstract: Catechol compounds of formula I ##STR1## where R.sub.1, R.sub.2, R.sub.3 and X are as described herein are effective Catechol-O-methyltransferase inhibitors.
    Type: Grant
    Filed: December 7, 1992
    Date of Patent: February 1, 1994
    Assignee: Orion-yhtyma Oy
    Inventors: Reijo J. Backstrom, Kalevi E. Heinola, Erkki J. Honkanen, Seppo K. Kaakkola, Pekka J. Kairisalo, Inge-Britt Y. Linden, Pekka I. Mannisto, Erkki A. O. Nissinen, Pentti Pohto, Aino K. Pippuri, Jarmo J. Pystynen
  • Patent number: 5237089
    Abstract: N-substituted 3,4,5,6-tetrahydrophthalimides and their intermediates of the general formula I ##STR1## where A is --NO.sub.2, --NH.sub.2 or ##STR2## corresponding to the compounds Ia, Ib and Ic, B is --CH.sub.2 --, --CH.sub.2 --CHR.sup.1 --, --CH.sub.2 --CHR.sup.1 --CH.sub.2 --, --CH.dbd., --CH.dbd.CR.sup.1 -- or --CH.dbd.CR.sup.1 --CH.dbd., R.sup.1 being --H, --Cl, --Br or --CH.sub.3, D is ##STR3## or .dbd.C<, depending on the terminal group B, X is --H, --Cl or --Br, Y is --H, C.sub.1 -C.sub.7 -alkyl, --Cl, --Br, --CN, --CONH.sub.2 or --CO.sub.2 R.sup.2, where R.sup.2 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylmercapto-C.sub.2 -C.sub.4 -alkyl, propargyl, benzyl, .alpha.-phenylethyl, .alpha.-phenylpropyl, C.sub.2 -C.sub.4 -alkyl which is monosubstituted, disubstituted or trisubstituted by F or Cl, or CH.sub.3 -substituted or Cl-substituted allyl, and Z is --COOR.sup.2, --CONR.sup.3 R.sup.4, ##STR4## or --COR.
    Type: Grant
    Filed: December 3, 1992
    Date of Patent: August 17, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Plath, Karl Eicken, Norbert Goetz, Jochen Wild, Norbert Meyer, Bruno Wuerzer
  • Patent number: 5206429
    Abstract: An improved all nitric acid nitration process for the nitration of phthalic acid, phthalic anhydrides and derivatives thereof wherein the improvement consists essentially of employing a rate enhancing amount of a nitration promoting inorganic acid anhydride to enhance the rate of nitration.
    Type: Grant
    Filed: July 13, 1989
    Date of Patent: April 27, 1993
    Assignee: General Electric Company
    Inventor: Roy R. Odle
  • Patent number: 5166377
    Abstract: The invention concerns novel 4-phenyl-1,3-dioxan-5-ylalkenoic acid derivatives of the formula I having cis relative stereochemistry at positions 4 and 5 of the dioxane ring and wherein Ra and Rb are variously hydrogen, alkyl, halogenoalkyl, alkenyl, and optionally substituted aryl or arylalkyl, Rc is hydroxy, alkoxy or alkanesulphonamido, n is 1 or 2, A is ethylene or vinylene, Y is (2-5C)polymethylene optionally substituted by alkyl, and benzene ring B is optionally substituted phenyl, or, when Rc is hydroxy, a salt thereof. The acid derivatives antagonize one or more of the actions of thromboxane A.sub.2 (TXA.sub.2) and are expected to be of value in those disease conditions in which TXA.sub.2 is involved. The invention also provides pharmaceutical compositions containing an acid derivative of formula I, and processes for their chemical production.
    Type: Grant
    Filed: February 9, 1988
    Date of Patent: November 24, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Andrew G. Brewster, Peter W. R. Caulkett
  • Patent number: 5155234
    Abstract: A process for the preparation of nitrophthalic acid by the nitration of phthalic acid and/or phthalic anhydride using only nitric acid, said nitric acid having a concentration of at least about 95% by weight, and then recovering the nitrophthalic acid formed from the nitric acid solution.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: October 13, 1992
    Assignee: General Electric Company
    Inventor: Roy R. Odle
  • Patent number: 5124471
    Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: June 23, 1992
    Assignee: The United States of America as represented by the Secretary of the Department of Health and Human Services
    Inventors: Otto A. Gansow, Martin W. Brechbiel
  • Patent number: 5112868
    Abstract: The present invention is novel selected hydroxamic acid derivatives of acyl residues of selected NSAIDS, i.e. having 5-lipoxygenase and cyclooxygenase inhibiting properties, pharmaceutical compositions for treating conditions advantageously affected by the inhibition and methods for treating these conditions in mammals, including humans suffering therefor.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: May 12, 1992
    Assignee: Warner-Lambert Company
    Inventors: Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Jagadish C. Sircar
  • Patent number: 5081263
    Abstract: The invention relates to the dioxane adducts of armoatic meta-or para-hydroxycarboxylic acids, which consist, per mole, of 1 mole of 1,4-dioxane and about 2 moles of hydroxycarboxylic acid. The invention further relates to a process for the preparation of these adducts, which comprises dissolving the hydroxycarboxylic acids in dioxane or a mixture of the latter with water or with an organic solvent and then allowing the adducts to crystallize.
    Type: Grant
    Filed: December 14, 1989
    Date of Patent: January 14, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: von Helmold Plessen, Siegbert Rittner
  • Patent number: 5055582
    Abstract: This invention relates to a process for preparing useful thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)thioxomethyl]hydrazono]ethyl]-1.alpha. ,4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha.,7a.alpha.-4.alpha.,7.alpha.-meth ano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: October 8, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 5041638
    Abstract: An alkenoic acid derivative of the formula ##STR1## in which X and Y are identical or different and represent sulfur, sulfoxide, sulfone, an alkylene chain, --SCH.sub.2 --, or oxygen or a direct bond,W represents --CH.dbd.CH-- or --CH.sub.2 --CH.sub.2 --,o represents a number 1 to 5,A and B are identical or different and represent carboxyl, carboxymethylene, tetrazolyl or tetrazolylmethylene, or --CO.sub.2 R.sup.9 or --CH.sub.2 CO.sub.2 R.sup.9 or --CONR.sup.10 R.sup.11 or nitrilen represents a number 1 to 10,m represents a number 0 to 7,T and Z are identical or different and represent oxygen or a direct bond andR.sup.2, R.sup.3, R.sup.8 are identical or different and represent hydrogen, alkyl, alkoxy, halogen, trifluoromethyl, trifluoromethoxy, cyano or nitro andR.sup.9 is lower alkyl and R.sup.10 and R.sup.11 are hydrogen, lower alkyl, alkylsulfonyl or arylsulfonyl or together are an alkylene chain to form a ringand pharmaceutically acceptable salts thereof.
    Type: Grant
    Filed: May 9, 1989
    Date of Patent: August 20, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
  • Patent number: 5004817
    Abstract: Compounds having the formula (I): ##STR1## wherein: M is an alkali or alkaline-earth metal or a C.sub.1 -C.sub.18 alkyl group;X is a group selected from --CH.sub.2 --, --CO--, --CH.sub.2 --CO--, --CH(CH.sub.3)--CO--,p is 0 or 1;Ar is a simple or condensed aromatic ring or Ar represents two or more aromatic nuclei bonded either by a simple bond or by an --O--, --S--, --SO.sub.2 --, --SO--, --CO--, --CS--, or --NH-- group;y is H or CH.sub.3 ;m is 1 when Y=--CH.sub.3, or an integer from 1 to 5 (including both values) when Y=H; n is a number ranging from 1 to 500 (including both values); andZ is H; a C.sub.1 -C.sub.18 alkyl; benzyl; glycidyl; acetyl; allyl; --CO--NH--R or --CO--NH--R.sub.1 --NCO group.
    Type: Grant
    Filed: February 27, 1989
    Date of Patent: April 2, 1991
    Assignee: Montefibre, S.p.A.
    Inventors: Catia Bastioli, Salvatore Garlisi, Dario Fornara, Vittorio Bellotti
  • Patent number: 4999429
    Abstract: Aryl difluoromethyl sulfone adds to aldehydes under phase transfer conditions to give novel substituted alcohols of the general formulaRCH(OH)CF.sub.2 SO.sub.2 Ar (I)wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
    Type: Grant
    Filed: November 13, 1989
    Date of Patent: March 12, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly