Nitro Or Nitroso Patents (Class 562/434)
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Patent number: 6271416Abstract: 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: GrantFiled: June 20, 2000Date of Patent: August 7, 2001Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Hidetsugu Takagaki, Shinobu Yamaguchi, Masayoshi Abe, Mitsuru Sakai, Osamu Misumi
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Publication number: 20010005762Abstract: 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) 1Type: ApplicationFiled: December 27, 2000Publication date: June 28, 2001Inventors: Tetsuya Shintaku, Masahide Tanaka, Nobushige Itaya
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Patent number: 6177463Abstract: The invention relates to new oxime derivatives, to a plurality of processes for their preparation, and to their use as pesticides.Type: GrantFiled: September 3, 1996Date of Patent: January 23, 2001Assignee: Bayer AktiengesellschaftInventors: 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
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Patent number: 6162943Abstract: 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: GrantFiled: April 16, 1999Date of Patent: December 19, 2000Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Albrecht Marhold
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Patent number: 6147224Abstract: 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: GrantFiled: October 1, 1998Date of Patent: November 14, 2000Assignee: Allergan Sales, Inc.Inventors: Vidyasagar Vuligonda, Kwok Yin Tsang, Jayasree Vasudevan, Roshantha A. Chandraratna
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Patent number: 6054609Abstract: 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: GrantFiled: November 19, 1998Date of Patent: April 25, 2000Assignee: Sumikin Chemical Co., Ltd.Inventors: Keiichi Yokota, Ikuo Ito, Seiji Takeuchi
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Patent number: 6048896Abstract: 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: GrantFiled: May 4, 1998Date of Patent: April 11, 2000Assignee: Pharmacia & Upjohn S.p.A.Inventors: Antonio Giordani, Paolo Pevarello, Carmela Speciale, Mario Varasi
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Patent number: 6028219Abstract: 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: GrantFiled: July 28, 1997Date of Patent: February 22, 2000Assignee: Zeneca LimitedInventors: John Heathcote Atherton, Stephen Martin Brown, James Peter Muxworthy, Martin Lennon
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Patent number: 5998661Abstract: A process for selective, direct oxidation of amine or amine hydrochloride mpounds is described. It uses mixed oxidizing agents of monopersulfate and ozone.Type: GrantFiled: June 15, 1998Date of Patent: December 7, 1999Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5990165Abstract: 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: GrantFiled: March 24, 1998Date of Patent: November 23, 1999Assignee: Lilly, S.A.Inventors: Concepcion Pedregal Tercero, Almudena Rubio Esteban
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Patent number: 5955505Abstract: 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: GrantFiled: August 20, 1997Date of Patent: September 21, 1999Assignee: Nippon Suisan Kaisha, Ltd.Inventors: Jiro Takeo, Shinya Yamashita, Keiji Wada, Yoshiyuki Chiba
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Patent number: 5952531Abstract: 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: GrantFiled: October 30, 1997Date of Patent: September 14, 1999Assignee: Zeneca LimitedInventors: Ian Jeffrey Grassham Priestley, James Peter Muxworthy, John Heathcote Atherton, Martin Lennon, Stephen Martin Brown
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Patent number: 5932763Abstract: 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: GrantFiled: May 15, 1997Date of Patent: August 3, 1999Assignee: Bayer CorporationInventors: William J. Scott, Margaret A. Popp, David S. Hartsough
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Patent number: 5932616Abstract: 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: GrantFiled: April 4, 1994Date of Patent: August 3, 1999Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia Univerisity in the City of New YorkInventors: Ronald Breslow, Paul A. Marks, Richard A. Rifkind, Branko Jursic
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Patent number: 5929117Abstract: 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: GrantFiled: August 11, 1997Date of Patent: July 27, 1999Assignee: Celgene CorporationInventors: George W. Muller, Mary Shire
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Patent number: 5869734Abstract: 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: GrantFiled: September 23, 1996Date of Patent: February 9, 1999Assignee: Bristol-Myers Squibb Co.Inventors: Xuebao Wang, John K. Thottathil
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Patent number: 5808003Abstract: A compound according to the formula: ##STR1## and conjugates thereof.Type: GrantFiled: September 18, 1996Date of Patent: September 15, 1998Assignee: PerImmune Holdings, Inc.Inventors: Ramaswamy Subramanian, James Colony
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Patent number: 5731454Abstract: 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: GrantFiled: January 18, 1995Date of Patent: March 24, 1998Assignee: Virginia Commonwealth UniversityInventors: Donald J. Abraham, Gajanan Joshi, Ramnarayan Randad, Jayashree Panikker
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Patent number: 5721234Abstract: 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: GrantFiled: October 23, 1995Date of Patent: February 24, 1998Assignee: Warner-Lambert CompanyInventors: Christopher Franklin Bigge, Daniel Martin Retz
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Patent number: 5719317Abstract: 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: GrantFiled: March 28, 1997Date of Patent: February 17, 1998Assignee: Rhone-Poulenc Rorer S.A.Inventor: Franco Manfre
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Patent number: 5719306Abstract: 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: GrantFiled: June 6, 1995Date of Patent: February 17, 1998Assignee: 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
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Patent number: 5698738Abstract: 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: GrantFiled: May 15, 1995Date of Patent: December 16, 1997Assignees: Board of Regents, The University of Texas System, The Texas A&M University SystemInventors: Robert E. Garfield, Alexandru T. Balaban, William A. Seitz, Douglas J. Klein, Melanie Lesko
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Patent number: 5688945Abstract: 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: GrantFiled: December 20, 1996Date of Patent: November 18, 1997Assignees: Astra Aktiebolag, The University of Maryland at BaltimoreInventors: Susanna Karin Maria Bjork, Birgitta Kristina Gotthammar, Mats Torbjorn Linderberg, Johan Per Luthman, Kerstin Margareta Irma Persson, Robert Schwarcz
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Patent number: 5635608Abstract: 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: GrantFiled: November 8, 1994Date of Patent: June 3, 1997Assignee: Molecular Probes, Inc.Inventors: Richard P. Haugland, Kyle R. Gee
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Patent number: 5610190Abstract: Urea-containing hydroxyethylamine compounds are effective as retroviral protease inhibitors, and in particular as inhibitors of HIV Protease.Type: GrantFiled: June 7, 1995Date of Patent: March 11, 1997Assignee: 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
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Patent number: 5599814Abstract: 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: GrantFiled: April 24, 1995Date of Patent: February 4, 1997Assignee: Imperial Chemical Industries, PLCInventors: Thomas M. Bare, Richard B. Sparks
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Patent number: 5523475Abstract: 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: GrantFiled: February 24, 1994Date of Patent: June 4, 1996Assignees: Aktiebolaget Astra, Cornell Research Foundation, Inc., The University of Maryland at BaltimoreInventors: Susanna K. M. Bjork, Barry K. Carpenter, Birgitta K. Gotthammar, Mats T. Linderberg, Johan P. Luthman, Kerstin M. I. Persson, Robert Schwarcz
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Patent number: 5514683Abstract: 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: GrantFiled: August 9, 1994Date of Patent: May 7, 1996Assignee: James Black Foundation LimitedInventors: 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
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Patent number: 5449809Abstract: 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: GrantFiled: July 30, 1993Date of Patent: September 12, 1995Assignee: BASF AktiengesellschaftInventors: Horst Wingert, Beate Hellendahl, Reinhard Kirstgen, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz
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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: 5442106Abstract: 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: GrantFiled: April 15, 1994Date of Patent: August 15, 1995Assignee: Indiana University FoundationInventors: Martel Zeldin, Wilmer K. Fife, Slawomir Rubinsztajn
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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: 5434287Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.Type: GrantFiled: November 4, 1993Date of Patent: July 18, 1995Assignee: The United States of America as represented by the Department of Health and Human ServicesInventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: 5430182Abstract: 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: GrantFiled: March 15, 1994Date of Patent: July 4, 1995Inventors: Claude Nofre, Jean-Marie Tinti
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Patent number: 5414108Abstract: 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: GrantFiled: August 11, 1992Date of Patent: May 9, 1995Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5350872Abstract: 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: GrantFiled: October 29, 1993Date of Patent: September 27, 1994Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5319122Abstract: 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: GrantFiled: November 12, 1992Date of Patent: June 7, 1994Assignee: Merck & Co., Inc.Inventor: Joel J. Friedman
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Patent number: 5288901Abstract: 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: GrantFiled: April 8, 1992Date of Patent: February 22, 1994Assignee: American Cyanamid CompanyInventors: Robert F. Doehner, Jr., Jerry M. Barton, David G. Kuhn
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Patent number: 5283352Abstract: 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: GrantFiled: December 7, 1992Date of Patent: February 1, 1994Assignee: Orion-yhtyma OyInventors: 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
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Patent number: 5237089Abstract: 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: GrantFiled: December 3, 1992Date of Patent: August 17, 1993Assignee: BASF AktiengesellschaftInventors: Peter Plath, Karl Eicken, Norbert Goetz, Jochen Wild, Norbert Meyer, Bruno Wuerzer
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Patent number: 5206429Abstract: 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: GrantFiled: July 13, 1989Date of Patent: April 27, 1993Assignee: General Electric CompanyInventor: Roy R. Odle
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Patent number: 5166377Abstract: 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: GrantFiled: February 9, 1988Date of Patent: November 24, 1992Assignee: Imperial Chemical Industries PLCInventors: Andrew G. Brewster, Peter W. R. Caulkett
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Patent number: 5155234Abstract: 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: GrantFiled: May 13, 1991Date of Patent: October 13, 1992Assignee: General Electric CompanyInventor: Roy R. Odle
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Patent number: 5124471Abstract: The subject matter of the present invention relates to bifunctional cyclohexyl DPTA ligands and methods for utilizing these compounds.Type: GrantFiled: March 26, 1990Date of Patent: June 23, 1992Assignee: The United States of America as represented by the Secretary of the Department of Health and Human ServicesInventors: Otto A. Gansow, Martin W. Brechbiel
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Patent number: 5112868Abstract: 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: GrantFiled: May 2, 1990Date of Patent: May 12, 1992Assignee: Warner-Lambert CompanyInventors: Wiaczeslaw A. Cetenko, David T. Connor, Daniel L. Flynn, Jagadish C. Sircar
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Patent number: 5081263Abstract: 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: GrantFiled: December 14, 1989Date of Patent: January 14, 1992Assignee: Hoechst AktiengesellschaftInventors: von Helmold Plessen, Siegbert Rittner
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Patent number: 5055582Abstract: 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: GrantFiled: December 13, 1988Date of Patent: October 8, 1991Assignee: National Research Development CorporationInventors: Robert B. Garland, Masateru Miyano
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Patent number: 5041638Abstract: 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: GrantFiled: May 9, 1989Date of Patent: August 20, 1991Assignee: Bayer AktiengesellschaftInventors: Ulrich Rosentreter, Harold C. Kluender, Trevor S. Abram, Peter Norman, Steven R. Tudhope
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Patent number: 5004817Abstract: 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: GrantFiled: February 27, 1989Date of Patent: April 2, 1991Assignee: Montefibre, S.p.A.Inventors: Catia Bastioli, Salvatore Garlisi, Dario Fornara, Vittorio Bellotti
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Patent number: 4999429Abstract: 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: GrantFiled: November 13, 1989Date of Patent: March 12, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly