Boron Acids Or Salts Thereof (i.e., Compounds Having -xh, Wherein X Is Chalcogen, Attached Directly To Boron By Nonionic Bonding And Wherein The Hydrogen May Be Replaced By A Group Ia Or Iia Light Metal, Or By Substituted Or Unsubstituted Ammonium) Patents (Class 562/7)
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Publication number: 20020115096Abstract: Disclosed is a modular fluorescence sensor having the following general formula: 1Type: ApplicationFiled: January 17, 2002Publication date: August 22, 2002Applicant: Beckman Coulter, Inc.Inventors: Susumu Arimori, Tony D. James
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Patent number: 6420597Abstract: A process for purifying formylphenylboronic acids of the formula (I) where the formyl function is located in the ortho, meta or para position relative to the boronic acid function, by dissolving the crude formylphenylboronic acids in an alkaline solvent having a pH in the range from 8 to 11 separating off the insoluble organic impurities and subsequently acidifying the alkaline boronic acid solution and separating off and working up the precipitated boronic acid. The crude formylphenylboronic acid is preferably dissolved in aqueous alkali metal or alkaline earth metal oxide, hydroxide, carbonate or phosphate solutions at temperatures in the range from 5 to 50° C. The formylphenylboronic acids obtained have a purity of ≧99% and are suitable as precursors for liquid-crystalline compounds, as liquid crystals or as constituents of liquid-crystalline mixtures or as pharmaceutical intermediates.Type: GrantFiled: July 2, 2001Date of Patent: July 16, 2002Assignee: Clariant GmbHInventors: Frank Vollmüller, Andreas Meudt, Stefan Scherer
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Patent number: 6387890Abstract: Compositions and methods for inhibiting arginase activity, including arginase activity in a mammal, are provided. Methods of making the compositions of the invention are also provided as are methods of using the compositions therapeutically. The compositions described herein are useful for alleviating or inhibiting a variety of arinase- and NO synthase-related disorders, including heart diseae, gastrointestinal motility disorders, and penile erectile dysfunction in humans.Type: GrantFiled: April 10, 2000Date of Patent: May 14, 2002Assignee: Trustees of the University of PennsylvaniaInventors: David Christianson, Ricky Baggio, Daniel Elbaum
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Publication number: 20020032339Abstract: The invention provides a process for covalently coupling organic compounds which comprises reacting an aromatic ring compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitabIe base. The invention also provides useful arylboron intermediates.Type: ApplicationFiled: December 18, 1998Publication date: March 14, 2002Inventors: SEBASTIAN MARIO MARCUCCIO, MARY RODOPOULOS, HELMUT WEINGOLD
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Publication number: 20020012631Abstract: This invention relates to novel highly functionalized phosphine ligands as ancillary ligands in radiopharmaceuticals. Also, this invention provides radiopharmaceuticals comprised of highly functionalized phosphine ligated 99mTc labeled HYNIC-conjugated biomolecules that selectively localize at sites of disease and thus allow an image to be obtained of the loci using gamma scintigraphy. The invention also provides methods of use of the radiopharmaceuticals as imaging agents for the diagnosis of cardiovascular disorders such as thromboembolic disease or atherosclerosis, infectious disease and cancer.Type: ApplicationFiled: April 5, 2001Publication date: January 31, 2002Inventor: Shuang Liu
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Publication number: 20020010332Abstract: A process for purifying formylphenylboronic acids of the formula (I) 1Type: ApplicationFiled: July 2, 2001Publication date: January 24, 2002Applicant: Clariant GmbHInventors: Frank Vollmuller, Andreas Meudt, Stefan Scherer
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Publication number: 20010056202Abstract: A method is provided for making substantially ether-free alkali metal tetrakis(pentafluorophenyl) borate salts from tetrakis(pentafluorophenyl) borate magnesium bromide and converting the alkali metal tetrakis(pentafluorophenyl) borate salts to essentially ether-free trityl tetrakis(pentafluorophenyl) borate.Type: ApplicationFiled: May 18, 2001Publication date: December 27, 2001Inventor: Michael Van Der Puy
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Patent number: 6288259Abstract: This invention describes a process for covalently coupling organic compounds which comprises reacting an olefinic compound having a halogen or halogen-like substituent at a coupling position with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base. The invention also describes a process for preparing alkene borate intermediates comprising reacting an olefinic compound having a halogen or halogen-like substituent with a diboron derivative in the presence of a Group VIII metal catalyst and a suitable base.Type: GrantFiled: March 6, 2000Date of Patent: September 11, 2001Assignee: Commonwealth Scientific and Industrial Research OrganisationInventors: Sebastian Mario Marcuccio, Mary Rodopoulos, Helmut Weigold
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Patent number: 6184363Abstract: The invention provides novel non-&bgr;-lactam inhibitors of &bgr;-lactamases. In particular, the invention provides such inhibitors which are boronic acids of formula (1) which is set forth in the specification. These compounds may be used with &bgr;-lactam antibiotics to treat &bgr;-lactam-antibiotic-resistant bacterial infections. These compounds are also antibacterial by themselves. Finally, the invention provides a pharmaceutical composition comprising these compounds.Type: GrantFiled: December 16, 1998Date of Patent: February 6, 2001Assignee: Northwestern UniversityInventors: Brian K. Shoichet, Grady Scott Weston
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Patent number: 6162941Abstract: Resins and carbon--carbon composites are formed from di(alken-1-yl) borinic acids and borinates, either as monomers or as nonpolymerizing additives in a monomer mixture, with the effect of sharply increasing the oxidative stability of the cured product. The compounds have the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are H, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.5 -C.sub.7 cycloalkenyl, aryl, (C.sub.1 -C.sub.6 alkyl)-substituted aryl, (C.sub.2 -C.sub.6 alkenyl)-substituted aryl, or (C.sub.2 -C.sub.6 alkynyl)-substituted aryl, at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 being other than H.Type: GrantFiled: July 29, 1998Date of Patent: December 19, 2000Assignee: Aerojet-General CorporationInventors: Stephen John Backlund, Robert Earl Olsen
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Patent number: 6124471Abstract: Reagents suitable for the modification of a bioactive species for the purpose of incorporating one or more phenyldiboronic acid (PDBA) moieties for subsequent conjugation to a different (or the same) bioactive species having one or more pendant boronic compound complexing moieties of the general formula of General Formula I, ##STR1## wherein group R is a reactive electrophilic or nucleophilic moiety suitable for reaction of the PDBA reagent with a bioactive species. Group Z is a spacer selected from a saturated or unsaturated chain up to about 0 to 6 carbon equivalents in length, an unbranched saturated or unsaturated chain of from about 6 to 18 carbon equivalents in length with at least one intermediate amide or disulfide moiety, and a polyethylene glycol chain of from about 3 to 12 carbon equivalents in length. Group Q is a linkage that includes one of amide, ether and thioether moieties.Type: GrantFiled: September 28, 1999Date of Patent: September 26, 2000Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Edward A. Kesicki, Kevin P. Lund, Karin A. Hughes
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Patent number: 6075126Abstract: Boron compound complexing reagents, boron compound complexes, and methods of synthesizing these reagents and complexes are disclosed. These reagents and complexes include those shown in General Formula CIII, General Formula CIV, and General Formula CVI. In one embodiment, the reagents of General Formula CIII may be used to produce, after condensation with a bioactive species (BAS), the reagent of General Formula CIV. The reagent of General Formula CIV may be used to form a complex with a boron compound, such as a complex shown in General Formula CVI.Type: GrantFiled: August 21, 1998Date of Patent: June 13, 2000Assignee: Prolinx, Inc.Inventors: Mark L. Stolowitz, Edward A. Kesicki, Kevin P. Lund, Karin A. Hughes
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Patent number: 6066730Abstract: Disclosed herein is a method for reducing the rate of degradation of proteins in an animal comprising contacting cells of the animal with certain boronic ester and acid compounds. Also disclosed herein are novel boronic ester and acid compounds, their synthesis and uses.Type: GrantFiled: May 26, 1998Date of Patent: May 23, 2000Assignee: ProScript, Inc.Inventors: Julian Adams, Yu-Ting Ma, Ross Stein, Matthew Baevsky, Louis Grenier, Louis Plamondon
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Patent number: 6060462Abstract: This invention relates to electrophilic dipeptide analogs conjugated to an N,N-disubstituted .alpha.-amino acid as inhibitors of trypsin-like serine protease enzymes.Type: GrantFiled: August 1, 1997Date of Patent: May 9, 2000Assignee: DuPont Pharmaceuticals CompanyInventors: Robert Anthony Galemmo, Jr., Matthew Mark Abelman, Eugene Cruz Amparo, John Matthew Fevig, Robert Madara Knabb, William Henry Miller, Gregory James Pacofsky, Patricia Carol Weber, Joseph Cacciola
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Patent number: 6037490Abstract: Novel compounds which are useful for boron neutron capture therapy (BNCT) are disclosed. The compounds comprise a stable boron-containing group and an aminocycloalkane carboxylic acid group or a boronated acyclic hydrocarbon-linked amino carboxylic acid. Methods for synthesis of the compounds and for use of the compounds in BNCT are disclosed.Type: GrantFiled: September 3, 1997Date of Patent: March 14, 2000Assignee: The University of Tennessee Research CorporationInventors: George W. Kabalka, Rajiv R. Srivastava
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Patent number: 6008406Abstract: The present invention relates to novel class of phenylboronic acid complexing reagents useful for the preparation of bioconjugates, and the method of making and using such reagents. In the present invention, in the place of prior art Avidin-Biotin and Digoxigenin-anti-Digoxigenin systems, phenylboronic acid complexing reagents are utilized in conjunction with phenylboronic acid reagents (many of which are known in the prior art) to facilitate chemical conjugation without the use of intermediary biological macromolecules. Reagents suitable for the modification of a bioactive species for the purpose of incorporating a phenylboronic acid complexing moiety for subsequent conjugation to a different bioactive species having pendant phenylboronic acid moieties are of General Formula I or General Formula II. ##STR1## wherein group X is selected from either H, OH, NH.sub.2, NHCH.sub.3, NHOH and NHOCH.sub.Type: GrantFiled: February 25, 1997Date of Patent: December 28, 1999Assignee: Prolinx, Inc.Inventor: Mark L. Stolowitz
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Patent number: 5814622Abstract: Compound of formula (I) ##STR1## in which: R.sub.1 and R.sub.2, which are identical or different, represent hydrogen or alkyl or alternatively R.sub.1 and R.sub.2 form, with the carbon atom which bears them, cycloalkyl,R.sub.3 represents hydrogen or alkyl, phenyl or benzyl,R.sub.4 represents:optionally substituted amino, optionally substituted amindino, optionally substituted guanidino, optionally substituted isothioureido, optionally substituted iminomethylamino, mercapto substituted with heterocyclic, or heterocyclic,R.sub.5 and R.sub.6 each represent hydrogen or alkyl, or ##STR2## forms a boronic ester of pinanediol, m represents an integer such that 0.ltoreq.m.ltoreq.6,n represents an integer such that 1.ltoreq.n.ltoreq.6,A represents any one of the following groups:* optionally substituted bicycloalkyl (C.sub.5 -C.sub.10)phenyl,* or a group of formula: ##STR3## A.sub.1 represents --CO--, --CS--, --SO.sub.Type: GrantFiled: February 27, 1997Date of Patent: September 29, 1998Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Philippe Gloanec, Christine Lila, Bernard Portevin, Tony Verbeuren, Alain Rupin, Serge Simonet
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Patent number: 5763238Abstract: This invention relates to novel chiral boronic acid compounds which are capable of binding to polyols, particularly to saccharides and are useful in the analysis or separation of diols.Type: GrantFiled: December 28, 1995Date of Patent: June 9, 1998Assignee: Research Development Corporation of JapanInventors: Tony James, Saman Sandanayake, Seiji Shinkai
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Patent number: 5739318Abstract: The present invention relates to labelling agents comprising non-proteinaceous boronic acid conjugates having absorption maxima at not less than 600 nm, said label being provided by e.g., an azine, triphenylmethane, cyanine or phthalocyanine dye. The labelling agents are useful in the estimation and quantification of cisdiols such as glycosylated haemoglobin, by virtue of the substantially total absence of overlap with the absorption spectrum of haemoglobin. Oxazine and thiazine dyes exhibiting similar absorption characteristics and containing other activated moieties are similarly useful labelling agents, especially in the presence of haemoglobin.Type: GrantFiled: July 12, 1993Date of Patent: April 14, 1998Assignee: Axis Research ASInventors: Frank Frantzen, Erling Sundrehagen
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Patent number: 5714509Abstract: A sialidase inhibitor of the shown formula I: ##STR1## where dashed lines d.sub.1 and d.sub.2, X.sub.1, R.sub.1, R.sub.2, R.sub.6, R.sub.3, R.sub.4 and R.sub.5 are as described in the specification; or an analog, pharmaceutically acceptable salt, or derivative of the inhibitor, with the proviso that the inhibitor is not HNBA GBA or Neu5Ac2en. The inhibitor in a composition with a pharmaceutically acceptable carrier. Methods of making a pharmaceutical composition of an acceptable carrier and the inhibitor. Methods of inhibiting sialidase and methods of treating and preventing bacterial or trypanosomal infection using the inhibitor.Type: GrantFiled: May 3, 1995Date of Patent: February 3, 1998Assignee: The University of AlabamaInventors: Ming Luo, Clinton L. White
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Patent number: 5702952Abstract: The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety;W.sup.1 is a *SO.sub.2 NR.sup.2, *CONR.sup.2 or *CH.sub.2 N.sup..sym. R.sup.2.sub.2 group bound at the *-marked atom to the phenyl ring;R.sup.1 is hydrogen or an electron withdrawing substituent group; andeach R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability.Type: GrantFiled: February 21, 1997Date of Patent: December 30, 1997Assignee: Axis Biochemicals ASAInventors: Erling Sundrehagen, Frank Frantzen
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Patent number: 5698538Abstract: Novel boronic acid and ester and carboxyl-modified amino acid compounds of the Formula I, which are inhibitors of trypsin-like enzymes, are disclosed :R.sup.1 --Z--CHR.sup.2 --A,where R.sup.1, Z, R.sup.2 arid A are defined within.Type: GrantFiled: July 26, 1996Date of Patent: December 16, 1997Assignee: The DuPont Merck Pharmaceutical CompanyInventors: Eugene Cruz Amparo, William Henry Miller, Gregory James Pacofsky, John Wityak, Patricia Carol Weber, John Jonas Vytautas Duncia, Joseph Basil Santella, III
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Patent number: 5643893Abstract: Novel N-substituted-(dihydroxyboryl)alkyl purine, indole and pyrimidine derivatives have been found to be useful as inhibitors of inflammatory cytokines. They can be used, inter alia, in the therapy of septic shock, cachexia, rheumatoid arthritis, inflammatory bowel disease, multiple sclerosis and AIDS. The compounds are typically prepared by reaction of an bromoalkyl boronic acid with the purine, indole or pyrimidine base.Type: GrantFiled: June 22, 1994Date of Patent: July 1, 1997Assignees: Macronex, Inc., University of North CarolinaInventors: Bradley J. Benson, Xiannong Chen, George J. Cianciolo, Jose-Luis Diaz, Khalid S. Ishaq, Susan L. Morris-Natschke, Ronald J. Uhing, Henry Wong
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Patent number: 5631364Abstract: The invention provides novel labelled boronic acid conjugates of formula ##STR1## (wherein V is a reporter moiety; W.sup.2 is a bond or an organic linker moiety;W.sup.1 is a *SO.sub.2 NR.sup.2, *CON.sup.2 or *CH.sub.2 N.sym.R.sup.2 .sub.2 group bound at the *-marked atom to the phenyl ring;R.sup.1 is hydrogen or an electron withdrawing substituent group; andeach R.sup.2 independently is hydrogen or an optionally hydroxylated and optionally C.sub.1-6 -alkoxylated C.sub.1-6 -alkyl group) and salts thereof, e.g. for use in assays for cis-diols such as glycated blood proteins, having enhanced water-solubility and storage stability.Type: GrantFiled: March 31, 1994Date of Patent: May 20, 1997Assignee: AXIS Biochemicals ASAInventors: Erling Sundrehagen, Frank Frantzen
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Patent number: 5488157Abstract: A compound having the formula: ##STR1## where R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen or C.sub.1 -C.sub.4 alkyl; n is 2-4; X is aryl, substituted aryl or C.sub.1 -C.sub.6 alkyl; Y is selected from the group consisting of hydrogen, amino acid, dipeptide or tripeptide linked through the C-terminal carboxylic acid, and amine protecting group is presented.Type: GrantFiled: May 4, 1995Date of Patent: January 30, 1996Assignee: The Procter & Gamble CompanyInventors: David W. Bjorkquist, Rajan K. Panandiker
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Patent number: 5444049Abstract: A compound of formula (I): ##STR1## in which: R.sub.1 represents hydrogen or acyl, alkyl, benzyl, alkoxycarbonyl, benzyloxycarbonyl, phenoxycarbonyl, 5-[(dimethyl)amino]naphthylsulfonyl, alkoxycarbonylmethyl or carboxymethyl,R.sub.2 represents hydrogen or phenyl, substituted or unsubstituted benzyl, 3-thienylmethyl, 2-pyridylmethyl, diphenylmethyl, fluorenyl, naphthylmethyl, benzocyclobutyl, (dicyclopropylmethyl)methyl, indanyl or (C.sub.3 -C.sub.7 cycloalkyl)methyl,R'.sub.2 represents hydrogen or benzylor alternativelyR.sub.2 and R'.sub.2 together represent C.sub.6 H.sub.5 --CH.dbd.,R.sub.3 represents substituted alkyl or guanidinophenyl, amidinophenyl, aminophenyl, guanidinobenzyl, amidinobenzyl, aminobenzyl or cycloalkyl,R.sub.4 and R.sub.5 each represent hydrogen or alkyl, or ##STR2## forms a boronic ester of pinanediol, A represents any one of the groups as defined in the description.Medicinal products.Type: GrantFiled: February 22, 1994Date of Patent: August 22, 1995Assignee: Adir et CompagnieInventors: Guillaume de Nanteuil, Christine Lila, Michel Laubie, Tony Verbeuren, Serge Simonet, Alain Rupin, Bernard Portevin
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Patent number: 5442100Abstract: A compound having the formula: ##STR1## where R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen or C.sub.1-C.sub.4 alkyl; n is 2-4; X is aryl, substituted aryl or C.sub.1-C.sub.6 alkyl; Y is selected from the group consisting of hydrogen, amino acid, dipeptide or tripeptide linked through the C-terminal carboxylic acid, and amine protecting group is presented.Type: GrantFiled: August 14, 1992Date of Patent: August 15, 1995Assignee: The Procter & Gamble CompanyInventors: David W. Bjorkquist, Rajan K. Panandiker
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Patent number: 5405598Abstract: Compounds of formula I and II ##STR1## in which B contains a carboranyl group and one of R.sub.3 and R.sub.4 is a carboranyl group or a boronic acid or ester are useful sensitizing agents for boron neutron capture therapy.Type: GrantFiled: February 24, 1992Date of Patent: April 11, 1995Inventors: Raymond F. Schinazi, Dennis C. Liotta
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Patent number: 5384410Abstract: A method for the removal of ester protecting groups from .alpha.-amino boronic acid is disclosed for the preparation of compounds of formula (II) belowR.sup.1 -X.sub.n -NHCH (R.sup.2)-B(OH).sub.Type: GrantFiled: March 24, 1993Date of Patent: January 24, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventor: Charles A. Kettner
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Patent number: 5338875Abstract: The present invention is directed to intermediates of the following formula which are useful in the preparation of Carbapenem-antibiotics ##STR1##Type: GrantFiled: November 19, 1992Date of Patent: August 16, 1994Assignee: Merck & Co., Inc.Inventors: Ann DeCamp, Ulf H. Dolling, Yulan Li, Dale L. Rieger, Nobuyoshi Yasuda, Lyndon C. Xavier
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Patent number: 5227474Abstract: The present invention provides bifunctional chelating agents comprising a unique substrate reactive moiety incorporated into a carboxymethyl arm of a polyaminopolycarboxylate chelating framework capable of forming stable complexes with metal ions.Type: GrantFiled: May 28, 1991Date of Patent: July 13, 1993Assignee: Abbott LaboratoriesInventors: David K. Johnson, Steven J. Kline
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Patent number: 5187157Abstract: Peptides comprising C-terminal boronic acid derivatives of lysine, ornithine, and arginine, homoarginine and corresponding isothiouronium analogs thereof, are reversible inhibitors of trypsin-like serine proteases such as thrombin, plasma kallikrein and plasmin.Type: GrantFiled: April 6, 1988Date of Patent: February 16, 1993Assignee: Du Pont Merck Pharmaceutical CompanyInventors: Charles A. Kettner, Ashokkumar B. Shenvi
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Patent number: 5169841Abstract: The invention relates to compounds of the formula 1 ##STR1## in which A.sup.1 denotes a radical of the formulae ##STR2## A.sup.2 is absent or represents a radical of the formula ##STR3## R.sup.2, R.sup.3 and R.sup.4 are as defined in the specification, and X and Y, independently of one another, represent --O-- or --NR.sup.13 --, and to the salts thereof. Also described is a process for the preparation of the compounds of the formula 1, corresponding pharmaceutical products, and the use thereof as medicines, and intermediates for the preparation of these compounds.Type: GrantFiled: November 3, 1988Date of Patent: December 8, 1992Assignee: Hoechst AktiengesellschaftInventors: Heinz-Werner Kleeman, Hansjorg Urbach, Dieter Ruppert, Bernward Scholkens
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Patent number: 5157149Abstract: A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-.alpha.-benzoylamino-4-boronocinnamic acid, asymmetrically hydrogenating the z-.alpha.Type: GrantFiled: June 4, 1991Date of Patent: October 20, 1992Assignee: The United States of America as represented by the United States Department of EnergyInventor: Edward G. Samsel
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Patent number: 5144063Abstract: Novel cesium hydroxytriphenylborates are described. The addition of hydroxytriarylborate ions to aqueous media containing cesium ions to form such compounds as a precipitate is useful, for example, in the removal of radioactive cesium from nuclear fission plant waste streams and from cesium ion containing solutions resulting from the digestion of cesium ores.Type: GrantFiled: July 12, 1991Date of Patent: September 1, 1992Inventor: Jeffrey M. Sullivan
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Patent number: 5068403Abstract: A process for the production of a boronic acid of formula III, ##STR1## in which an organometallic of formula IV, ##STR2## in which formula IV, M represents a metallic moiety such as --MgX, X being a halogen or an alkali metal is treated with a trialkoxy borane of formula B(OR).sub.3, R representing an alkyl group and the product is hydrolyzed.Type: GrantFiled: October 27, 1989Date of Patent: November 26, 1991Assignee: National Research Development CorporationInventors: Michael Elliott, Norman F. Janes, Bhupinder P. S. Khambay