Halogen Patents (Class 562/438)
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Patent number: 4990661Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: March 29, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
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Patent number: 4933367Abstract: This invention relates to carboxylic acid derivatives and their use thereof. The compounds are useful in treatment of various diseases such as diabetes, prediabetic conditions, adipositas ailments or atherosclerosis.Type: GrantFiled: March 12, 1987Date of Patent: June 12, 1990Assignee: Boehringer Mannheim GmbHInventors: Hans P. Wolff, Ernst-Christian Witte, Hans-Frieder Kuhnle
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Patent number: 4876376Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.Type: GrantFiled: December 15, 1987Date of Patent: October 24, 1989Assignee: Rhone-Poulenc Specialistes ChimiquesInventors: Michael Desbois, Camille Disdier
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Patent number: 4868347Abstract: Substituted fluorobenzenes which are produced in aprotic, polar solvents or in mixtures which contain such solvents can be obtained by extracting the substituted fluorobenzenes from the solvents or solvent mixtures with aliphatic extracting agents and then seaprating the extracting agents from the substituted fluorobenzenes.Type: GrantFiled: December 9, 1987Date of Patent: September 19, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Edwin Ritzer
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Patent number: 4868333Abstract: 2-Nitro-4-trifluoromethylbenzoic acid is produced by hydrolysis of 2-nitro-4-trifluoromethylbenzonitrile in the presence of relatively concentrated hydrochloric or hydrobromic acid under reflux temperature.Type: GrantFiled: November 16, 1987Date of Patent: September 19, 1989Assignee: ICI Americas Inc.Inventors: Stephen E. Dinizo, Richard D. Gless, Jr.
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Patent number: 4845279Abstract: An isomer mixture of 4-trifluoromethyl-2-nitrobenzoic acid and 4-trifluoromethyl-3-nitrobenzoic acid, which is a novel compound, is obtained by nitrating a compound represented by ##STR1## (Z is COY or CY.sub.3, and Y is a halogen atom) with a nitrating agent comprising nitric acid and simultaneously hydrolyzing the radical Z. Each of the two isomers is easily isolated by treating the mixture with a basic neutralizing agent to obtain a solution containing the 2-nitro isomer and a precipitate containing the 3-nitro isomer.Type: GrantFiled: December 22, 1987Date of Patent: July 4, 1989Assignee: Central Glass Company, LimitedInventors: Yasunori Nishimura, Yoshihiko Gotoh, Toshikazu Kawai
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Patent number: 4835306Abstract: This invention is a process for the preparation of a 3-amino-4-hydroxybenzoic acid which comprises(a) contacting a p-halobenzoic acid with nitric acid in an acidic reaction medium under conditions such that a 3-nitro-4-halobenzoic acid is prepared;(b) contacting the 3-nitro-4-halobenzoic acid with an alkali metal hydroxide in a reaction medium under conditions such that the halo moiety is replaced with a hydroxide moiety, to prepare a 3-nitro-4-hydroxybenzoic acid, or salt thereof; and(c) reducing the 3-nitro-4-hydroxybenzoic acid under conditions such that a 4-hydroxy-3-aminobenzoic acid is prepared.Type: GrantFiled: February 10, 1986Date of Patent: May 30, 1989Assignee: The Dow Chemical CompanyInventor: Zenon Lysenko
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Patent number: 4772744Abstract: Compounds of the formula ##STR1## wherein X is a hydrogen atom, a halogen atom, a trihalomethyl group, an alkyl group, or a cyano group,Y is a hydrogen atom, a halogen atom, or a trihalomethyl group, andZ is a substituted alkoxy group,and compositions containing these compounds exhibit herbicidal activity.Type: GrantFiled: April 27, 1987Date of Patent: September 20, 1988Assignee: Rohm and Haas CompanyInventors: Horst O. Bayer, Colin Swithenbank, Roy Y. Yih
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Patent number: 4727180Abstract: Polyhalohydroxyisopropyl phenylalkanoic and phenylalkenoic acids, amides, and esters, such as methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepro panoate, are useful as antihypertensive agents.Type: GrantFiled: January 4, 1985Date of Patent: February 23, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul E. Aldrich, Gilbert H. Berezin
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Patent number: 4614806Abstract: Disclosed herein is a process for producing an asymmetric indoline-2-carboxylic acid of the structural Formula: ##STR1## wherein X is hydrogen, bromine, chlorine, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, which comprises:(a) assymetrically reducing an o-nitrophenylpyruvic acid III by contacting the acid III with a reducing complex formed from (R)-proline or (S)-proline, respectively, and sodium borohydride in an inert solvent to form, respectively, an (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid IV;(b) reacting, respectively, said (S) or (R)-.alpha.-hydroxy-2-nitrobenzenepropanoic acid III with a Vilsmeier chlorinating reagent in which the chlorinating agent thereof is selected from a group consisting of thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride and sulfuryl chloride and the amide thereof is selected from a group consisting of dimethylformamide, diethylformamide, dimethylacetamide and diethylacetamide, said reaction being run at temperatures of at least 20.Type: GrantFiled: February 11, 1985Date of Patent: September 30, 1986Assignee: American Home Products CorporationInventors: George C. Buzby, Jr., Michael W. Winkley, Ronald J. McCaully
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Patent number: 4604243Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.Type: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4585879Abstract: Disclosed herein is a process for obtaining indoline-2-carboxylic acid (or derivatives thereof) comprising the following steps: (a) reducing .alpha.-oxo-2-nitrobenzenepropanoic acid to .alpha.-hydroxy-2-nitrobenzenepropanoic acid, (b) replacing the hydroxyl group of the latter with a chlorine atom utilizing a selected Vilsmeier chlorinating reagent at temperatures of at least 20.degree. C., (c) reducing the nitro group of the resulting .alpha.-chloro-2-nitrobenzenepropanoic acid to obtain .alpha.-chloro-2-aminobenzenepropanoic acid, and (d) cyclizing the latter in aqueous base to form the desired indoline-2-carboxylic acid. Alternately, steps (c) and (d) may be combined in a one pot step by using, for example, a Raney nickel-hydrazine reducing medium.Type: GrantFiled: February 11, 1985Date of Patent: April 29, 1986Assignee: American Home Products CorporationInventors: Michael W. Winkley, Ronald J. McCaully
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Patent number: 4581178Abstract: Low valent transition metal complexes containing small cone angle phosphine or arsine ligands efficiently catalyze addition of aldehydes to compounds or groups having a C--H bond activated by a nitro or nitrile group, to provide nitroalcohols or cyanohydrins, respectively.Type: GrantFiled: February 28, 1985Date of Patent: April 8, 1986Assignee: E. I. Du Pont de Nemours and CompanyInventor: David Milstein
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Patent number: 4504671Abstract: Aldoxime or ketoxime-O-alkanoic acid is prepared by transoximation of an aldehyde or ketone, the reaction being conducted in a liquid phase at a pressure below one atmosphere. Conversion of the aldoxime or ketoxime-O-alkanoic acid to the ester or salt form is also described.Type: GrantFiled: October 15, 1982Date of Patent: March 12, 1985Assignee: PPG Industries, Inc.Inventors: Dennis K. Krass, John C. Crano, Melvin S. Newman
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Patent number: 4499299Abstract: Compounds which antagonize the slow-reacting substance of anaphylaxis or components thereof, e.g., leukotrienes, in warm blooded animals as well as intermediates and methods for their preparation, pharmaceutical compositions and methods for their administration. The compounds are diphenyl carboxylic acids with particular linking groups between the individual phenyl rings and the carboxylic acid moiety. Particular utilities are to relieve asthma and inflammation in man.Type: GrantFiled: December 6, 1982Date of Patent: February 12, 1985Assignee: ICI Americas Inc.Inventors: Peter R. Bernstein, Alvin K. Willard
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Patent number: 4485254Abstract: This process relates to the oxidation of phenoxytoluenes to phenoxybenzoic acids utilizing a hydrogen peroxide activated, bromide promoted cobalt catalyst which can be performed at atmospheric pressure and at moderate temperatures. These phenoxybenzoic acids can then be esterified and selectively nitrated to give the corresponding 2-nitro-5-(substituted)phenoxybenzoic acid esters. Alternatively the acids can be nitrated and then esterified.Type: GrantFiled: September 30, 1981Date of Patent: November 27, 1984Assignee: Rohm and Haas CompanyInventor: Charles M. Tanger
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Patent number: 4477556Abstract: A photopolymerizable coating composition comprising(1) a nongaseous, ethylenically unsaturated, polymerizable compound,(2) a specified acidic o-nitroaromatic compound, and(3) an organic, radiation-sensitive, free-radical generating system which is useful for making a positive or negative polymeric image on a substrate.Type: GrantFiled: August 18, 1982Date of Patent: October 16, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thomas E. Dueber, William J. Nebe
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Patent number: 4476315Abstract: Nitroarylacetic acid esters are prepared by reacting a nitroaromatic compound which is devoid of halogen on the aromatic ring carrying a nitro group with an alpha,alpha-disubstituted acetic acid ester in an inert solvent and in the presence of a base so that the ester undergoes a nucleophilic substitution on an unsubstituted ring carbon of the nitroaromatic compound during which an alpha-substituent functions as a leaving group. Nitrobenzene acetic acids and their esters are useful intermediates for the synthesis of pharmaceuticals.Type: GrantFiled: December 23, 1982Date of Patent: October 9, 1984Assignee: Ethyl CorporationInventors: G. Patrick Stahly, Barbara C. Stahly
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Patent number: 4401828Abstract: This process relates to the oxidation of phenoxytoluenes to phenoxybenzoic acids utilizing a hydrogen peroxide activated, bromide promoted cobalt catalyst which can be performed at atmospheric pressure and at moderate temperatures. These phenoxybenzoic acids can then be esterified and selectively nitrated to give the corresponding 2-nitro-5-substituted)phenoxybenzoic acid esters. Alternatively the acids can be nitrated and then esterified.Type: GrantFiled: September 10, 1979Date of Patent: August 30, 1983Assignee: Rohm and Haas CompanyInventor: Charles M. Tanger
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Patent number: 4390702Abstract: A 3-substituted-3-fluoropyruvic acid and its ester and salt of the formula: ##STR1## wherein R is a lower alkyl group, a lower alkanoyl group, a fluorinated lower alkanoyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group and R' is a hydrogen atom, an ester-forming residue or a salt-forming residue, and their production.Type: GrantFiled: December 29, 1980Date of Patent: June 28, 1983Assignees: Daikan Kogyo Co., Ltd., Shionogi and Co., Ltd.Inventors: Susumu Misaki, Masahiro Suefuji, Tadahiko Tsushima, Hiroshi Tanida
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4371547Abstract: 2-Benzylideneglutaraldehydes of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 independently are hydrogen or a substituent selected from the group consisting of halo, lower-alkyl, phenyl, carboxy, lower-alkoxycarbonyl, phenoxycarbonyl, aminocarbonyl, hydroxysulfonyl, nitro, cyano, hydroxy, lower-alkoxy and phenoxy, a method of use thereof as disinfectants, disinfectant compositions comprising them, and 2,6-dialkoxy-3-(.alpha.-alkoxybenzyl)tetrahydropyrans of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are as defined above and R.sup.4 and R.sup.5 independently are alkyl of one to four carbon atoms, which are intermediates for their preparation are disclosed.Type: GrantFiled: August 21, 1981Date of Patent: February 1, 1983Assignee: Sterling Drug Inc.Inventors: Wolfgang Munzenmaier, Heinz Eggensperger, Helmut H. Ehlers, Wolfgang Beilfuss, Lothar Bucklers, Hans-Peter Harke
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Patent number: 4351950Abstract: Novel substituted arylene compounds and methods for their preparation and use are disclosed. These new compounds are useful as anti-arteriosclerotic agents.Type: GrantFiled: January 2, 1980Date of Patent: September 28, 1982Assignee: Warner-Lambert CompanyInventor: Ila Sircar
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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Patent number: 4339601Abstract: The novel compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each either hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and maybe the same or different, are useful intermediates in a novel process for the preparation of herbicidally active compounds such as 2,5-dichloro-3-nitro-benzoic acid, 2,5-dichloro-3-amino-benzoic acid and their functional derivatives.Type: GrantFiled: September 30, 1980Date of Patent: July 13, 1982Assignee: Union Carbide CorporationInventor: Albert M. V. Jacques
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Patent number: 4338316Abstract: The disclosure relates to 9.beta.-aryloxy prostane derivatives, for example 16-(3-chlorophenoxy)-11.alpha.,15.alpha.-dihydroxy-16-methyl-9.beta.-pheno xy-18,19,20-trinor-5-cis,13-trans-prostadienoic acid, which possess high activity as abortifacients, cervical softeners, inducers of parturition or inhibitors of gastric acid production in mammals. These properties are typical of prostaglandin analogues of the E series, but chemically the new 9.beta.-aryloxy prostane derivatives are prostaglandin F series analogues and are therefore more stable than the E series analogues previously used for the above purposes. The new derivatives are manufactured by known analogy processes, and are formulated in conventional manner.Type: GrantFiled: September 26, 1979Date of Patent: July 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Peter R. Marsham
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Patent number: 4304728Abstract: Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.Type: GrantFiled: March 27, 1980Date of Patent: December 8, 1981Assignee: Lilly Industries LimitedInventors: Barry P. Clark, William J. Ross, Alec Todd
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Patent number: 4287125Abstract: Benzenoid ethers/thioethers are prepared by reacting an activated halobenzene with an anionic reactant, RA.sup.- M.sup.+, in the presence of at least one tertiary amine sequestering agent having formula:N--CHR.sub.1 --CHR.sub.2 --O--CHR.sub.3 --CHR.sub.4 --O--.sub.n R.sub.5 ].sub.Type: GrantFiled: June 20, 1980Date of Patent: September 1, 1981Assignee: Rhone-Poulenc IndustriesInventor: Gerard Soula
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Patent number: 4266060Abstract: The invention relates to compounds of formula: ##STR1## wherein R'.sub.1 =H, OH or an alkyl group, preferably a lower alkyl group, alkylthio or alkoxy, an halogen or an amino group,R'.sub.2 =H or a lower alkyl group.These compounds have antitumoral and antiviral properties useful for the treatment of cancers.Type: GrantFiled: April 13, 1978Date of Patent: May 5, 1981Assignee: Agence Nationale de Val orisation de la Recherche (ANVAR)Inventors: Emile Bisagni, Claire Ducrocq, Christian Rivalle, Pierre Tambourin, Francoise Wendling, Jean-Claude Chermann, Luc Montagnier
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Patent number: 4259510Abstract: A process for preparing trifluoromethylphenyl nitro phenylethers which comprises treating a trifluoromethylhalobenzene with a base in a cosolvent system to afford a trifluoromethyl phenolate which may be isolated as its free phenol or reacted with an appropriately substituted halobenzene to afford a diphenylether herbicide or a precursor thereto.Type: GrantFiled: May 19, 1980Date of Patent: March 31, 1981Assignee: Rohm and Haas CompanyInventor: Wayne O. Johnson
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Patent number: 4252979Abstract: The novel compounds of the formula: ##STR1## wherein R.sup.1 and R.sup.2 are each either hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and maybe the same or different, are useful intermediates in a novel process for the preparation of herbicidally active compounds such as 2,5-dichloro-3-nitro-benzoic acid, 2,5-dichloro-3-amino-benzoic acid and their functional derivatives.Type: GrantFiled: January 26, 1979Date of Patent: February 24, 1981Assignee: Amchem Products Inc.Inventor: Albert M. V. Jacques
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Patent number: 4228304Abstract: The present invention relates to novel cyclohexanecarboxylic acid and its derivatives represented by the general formula: ##STR1## (wherein R.sup.1 is selected from the group consisting of hydrogen or methyl; R.sup.2 is selected from the group consisting of hydroxyl, lower alkoxy with 1-6 carbons or amino acid rest. In case R.sup.1 is hydrogen, however, R.sup.Type: GrantFiled: April 11, 1978Date of Patent: October 14, 1980Assignee: Hisamitsu Pharmaceutical Co. Inc.Inventors: Kanji Noda, Akira Nakagawa, Kenji Yamagata, Terumi Hachiya, Hiroyuki Ide, Akihide Koda
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Patent number: 4218368Abstract: Aromatic nitro compounds are disclosed where the aromatic ring contains electron-withdrawing groups and said aromatic nitro compound is capable of undergoing intramolecular nucleophilic displacement after reduction of the nitro group. The compounds are especially useful in photographic elements where an image dye-providing material or a photographic reagent are released upon cleavage from the compound.Type: GrantFiled: July 26, 1978Date of Patent: August 19, 1980Assignee: Eastman Kodak CompanyInventors: Jerald C. Hinshaw, Richard P. Henzel
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Patent number: 4199595Abstract: The invention is m-phenoxybenzyl esters of 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful insecticidal and acaricidal agents.Type: GrantFiled: March 20, 1978Date of Patent: April 22, 1980Assignee: American Cyanamid CompanyInventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4189605Abstract: The invention is addressed to the preparation of 3-nitro-4-bromomethyl benzoic acid, as a new compound from which 3-nitro-4-bromomethyl benzoyl amide polystyrene resin can be prepared for solid synthesis of protected peptide acids and amides and separation thereof without cleavage of acid labile protecting groups or decomposition of aromatic acid groups and from which purified polypeptides can be formed.Type: GrantFiled: November 10, 1977Date of Patent: February 19, 1980Assignee: Wisconsin Alumni Research FoundationInventors: Daniel H. Rich, Sweet K. Gurwara
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Patent number: 4182905Abstract: Organic compounds having a substituent represented by the formula ##STR1## wherein M is alkali metal or ammonium are useful complexing agents for metal and/or alkaline earth metal ions.Type: GrantFiled: September 2, 1977Date of Patent: January 8, 1980Assignee: Monsanto CompanyInventor: Kent P. Lannert
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Patent number: 4178460Abstract: The invention is 2-haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids which are useful intermediates in the preparation of insecticides of m-phenoxybenzyl and .alpha.-cyano-m-phenoxybenzyl esters.Type: GrantFiled: March 20, 1978Date of Patent: December 11, 1979Assignee: American Cyanamid Co.Inventors: Gerald Berkelhammer, Venkataraman Kameswaran
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Patent number: 4172098Abstract: Halobenzenes are manufactured by (a) a one-vessel reaction of anilines with halogenating agents to give haloanilines, followed by reaction of the mixture thus obtained with alkanols and nitrosylating agents in the presence of water and acid at not less than 35.degree. C. or (b) the corresponding reaction of a haloaniline which has been manufactured in the above manner or by some other method and has been isolated from its reaction mixture. The products are starting materials for the manufacture of drugs, dyes and pesticides.Type: GrantFiled: November 15, 1977Date of Patent: October 23, 1979Assignee: BASF AktiengesellschaftInventors: Horst Scheuermann, Ulrich Jersak, Helmut Gorth
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Patent number: 4154961Abstract: Anti-allergic agents of aromatic oxamic acid derivation present the following formula: ##STR1## in which A is a member selected from the group consisting of .alpha.-naphthyl, .beta.-naphthyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals;And pharmaceutically acceptable salts thereof.Type: GrantFiled: September 19, 1977Date of Patent: May 15, 1979Assignee: American Home Products CorporationInventors: John H. Sellstedt, Charles J. Guinosso, Albert J. Begany
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Patent number: 4120867Abstract: Monoradioiodinated derivatives of compounds employed in a radioassay prepared from precursors which are either active esters, amino acids, or amines, including a phenolic or imidazole substituent group in which one of the possible two sites on the group for radioiodination is substituted to permit production of a monoradioiodinated derivative. A preferred precursor is an active ester of 3-fluoro-5-radioidotyrosine which can be coupled to a compound including an amino group to produce a monoradioiodinated derivative of the compound.Type: GrantFiled: September 29, 1976Date of Patent: October 17, 1978Assignee: Becton, Dickinson & CompanyInventors: Anandrao S. Akerkar, Herman Rutner