Benzene Ring Containing Patents (Class 568/424)
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Patent number: 4605777Abstract: This invention relates to a method of manufacturing ortho- and para-nitrobenzaldehyde from o-chloro or o-bromobenzaldehyde and p-chloro or p-bromobenzaldehyde respectively through a nucleophilic aromatic substitution reaction performed in an organic solvent.Type: GrantFiled: June 12, 1985Date of Patent: August 12, 1986Assignee: Nobel Kemi ABInventor: Boris Holm
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Patent number: 4605749Abstract: There is provided a process for the production of aldehydes wherein an oric halide is reacted with carbon monoxide at a superatmospheric pressure in the presence of a hydrogen donor and in the presence of a base and of a catalyst in a solvent system.Catalysts of choice are transition metal catalysts. A preferred temperature range is from about 50.degree. to 150.degree. C.Type: GrantFiled: June 20, 1985Date of Patent: August 12, 1986Assignee: State of Israel, Prime Minister's Office, Atomic Energy CommissionInventors: Ouri Buchman, Ilan Pri-Bar
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Patent number: 4603222Abstract: Diphenyl ethers of the formula ##STR1## wherein m is 1-3, n is 1 or 2, R is hydrogen, carboxy, carboxylate salt or ester, formyl oxime, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride of the formula ##STR2## wherein m and n are as defined above with a nitro-phenoxide of the formula ##STR3## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.Type: GrantFiled: August 30, 1984Date of Patent: July 29, 1986Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
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Patent number: 4593029Abstract: Novel compound of the formula ##STR1## wherein n is an integer of 1 to 8;R.sub.1 is hydrogen or alkyl of 1-6 carbons;R.sub.2 is hydrogen;R.sub.3 is hydrogen, alkyl of 1-6 carbons, phenyl, benzyl, hydroxy lower alkyl, carbamoyl alkyl, carboxyalkyl, alkoxycarbonylalkyl;R.sub.4 is hydrogen, alkyl of 1-6 carbons, benzyl, or hydroxy lower alkyl;Y is hydrogen, alkyl of 1 to 4 carbon atoms, halo or lower alkoxy;any of its optical isomers, the mixture thereof, or the pharmaceutically acceptable acid addition salt.These compounds are inhibitors of thromboxane synthetase and cyclic AMP phosphodiesterase and are therefore potential cardiovascular agents particularly useful as platelet aggregation inhibitors and anti-thrombotic agents. Accordingly, these compounds will preferably be useful in treating cardiovascular disorders with thrombotic complications. However, they also possess vasodilatory, antisecretory, antihypertensive, inotropic and antimetastatic activities.Type: GrantFiled: February 15, 1984Date of Patent: June 3, 1986Assignee: Syntex (U.S.A.) Inc.Inventors: Michael C. Venuti, John J. Bruno
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Patent number: 4544765Abstract: Chloramphenicol derivatives are provided for use in the preparing of antigen conjugates for the production of antibodies specifically for chloramphenicol. Specifically, the aryl amino group is derivatized to introduce a non-oxocarbonyl group which is used for amide formation with an antigen. The conjugate is then injected into a vertebrate for production of antisera which is isolated in conventional ways and find particular use in competitive protein binding assays.Type: GrantFiled: November 30, 1984Date of Patent: October 1, 1985Assignee: Syra CompanyInventors: Pyare Khanna, Evan S. Snyder, Prithipal Singh
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Patent number: 4542233Abstract: Improvement in the process for preparing biaryl compounds via coupling of an arylamine with an arene in the presence of a nitrite, an acid and copper metal or a derivative thereof; the improvement is consisting in adding to the reaction mixture a trialkylorthoformate. The process may be used for preparing drugs such as Flurbiprofen and Xenbucin or intermediate compounds particularly useful for preparing Flurbiprofen, Flufenisal, Chlordimorin, Xenbucin, Xenysalate, Xenyhexenic acid and the like.Type: GrantFiled: July 20, 1983Date of Patent: September 17, 1985Assignee: Biaschim S.p.A.Inventors: Oreste Piccolo, Aldo Belli, Giovanni Villa, Enrico Zen, Attilio Citterio
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Patent number: 4540828Abstract: Catalysts and a method of using said catalysts for the alkoxylation of a variety of materials is disclosed. Catalysts so described produce alkoxylates having a very sharp alkoxylate distribution. The catalysts are supported and unsupported dialkoxy and dialkyl metal fluorides and halides and alkyl metal difluorides and dihalides.Type: GrantFiled: February 25, 1983Date of Patent: September 10, 1985Assignee: Vista Chemical CompanyInventor: Kang Yang
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Patent number: 4533754Abstract: A process for the preparation of aldehydes of the formula ##STR1## wherein R is a substituted or unsubstituted aryl group containing one or more benzenoid rings which comprises reacting an aryl acid halide with an organozinc compound in solvent in the presence of a palladium metal complex catalyst.Type: GrantFiled: July 23, 1984Date of Patent: August 6, 1985Assignee: Atlantic Richfield CompanyInventor: Roger A. Grey
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Patent number: 4532363Abstract: There is a method for the production of 3-phenylpyrrole derivatives having the general formula ##STR1## wherein X is halogen, nitro or haloalkyl having 1 to 3 carbon atoms;n is 0, 1 or 2; andZ is hydrogen or halogen;which comprises reacting a compound having the general formula ##STR2## wherein X and n are as previously defined; andY is hydrogen or halogen;with ammonia or aqueous ammonia in an organic solvent.A compound having the general formula [I] is useful as fungicide or intermediate thereof.Type: GrantFiled: May 30, 1984Date of Patent: July 30, 1985Assignee: Nippon Soda Company LimitedInventors: Akiyoshi Ueda, Humiko Nagasaki, Yutaka Takakura, Shigeru Kojima
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Patent number: 4521630Abstract: Aldehydes are prepared by hydrogenating a compound of general formula R'COOR, wherein R represents a hydrogen atom, an alkyl or an acyl group, or a metal, and R' represents an optionally substituted hydrocarbyl group having at most two alpha-hydrogen atoms, provided it has at most one beta-hydrogen atom, in case it has two alpha-hydrogen atoms, in the presence of a catalyst comprising at least one metal selected from rare earth metals and iron on an alumina-based carrier.Type: GrantFiled: August 9, 1983Date of Patent: June 4, 1985Assignee: Shell Oil CompanyInventors: Freddy Wattimena, Hendricus J. Heijmen
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Patent number: 4503276Abstract: This invention pertains to a process for separating nitration isomers of 1,3-disubstituted and 1,2,4-trisubstituted benzene compounds. The separated isomers have a variety of uses including precursors for 2-haloacetanilide herbicides.Type: GrantFiled: January 9, 1984Date of Patent: March 5, 1985Assignee: Monsanto CompanyInventor: Thomas E. Nickson
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Patent number: 4482736Abstract: Herbicidally active compounds of the formula ##STR1## in which R.sup.1 represents a hydrogen or chlorine atom,R.sup.2 represents a hydrogen atom, a cyano group, an optionally substituted radical selected from alkyl, aryl, alkanoyl, benzoyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl, aralkoxycarbonyl and aryloxycarbonyl, or a radical of the general formula--COOM,in whichM represents a hydrogen atom, one equivalent of an alkali metal ion or alkaline earth metal ion or optionally substituted ammonium, andR.sup.3 represents a cyano group or a radical of the general formula ##STR2## wherein Y represents an oxygen or sulphur atom or an imino (NH) or alkylimino (Nalkyl) group,R.sup.4 and R.sup.5 independently of each other represent a hydrogen atom or a methyl group,n is 0 or 1 andZ represents an optionally substituted radical,Novel intermediates therefor are also shown.Type: GrantFiled: July 14, 1983Date of Patent: November 13, 1984Assignee: Bayer AktiengesellschaftInventors: Heinz Forster, Ludwig Eue, Robert Schmidt
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Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4471126Abstract: There is a method for the production of 3-phenylpyrrole derivatives having the general formula ##STR1## wherein X is halogen, nitro or haloalkyl having 1 to 3 carbon atoms;n is 0, 1 or 2; andZ is hydrogen or halogen;which comprises reacting a compound having the general formula ##STR2## wherein X and n are as previously defined; andY is hydrogen or halogen;with ammonia or aqueous ammonia in an organic solvent.A compound having the general formula [I] is useful as fungicide or intermediate thereof.Type: GrantFiled: April 18, 1983Date of Patent: September 11, 1984Assignee: Nippon Soda Company LimitedInventors: Akiyoshi Ueda, Humihiko Nagasaki, Yutaka Takakura, Shigeru Kojima
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Patent number: 4469893Abstract: Diphenyl esters of the formula ##STR1## wherein R is hydrogen, carboxy, carboxylate salt or ester, formyl, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride with a nitro-phenoxide of the formula ##STR2## where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.Type: GrantFiled: March 22, 1982Date of Patent: September 4, 1984Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Frederick J. Goetz
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Patent number: 4463195Abstract: Ortho-nitrobenzaldehyde, a well known compound suitable as an indicator and as an intermediate for many organic syntheses including production of pharmaceuticals, is obtained by contacting a C.sub.1 -C.sub.4 lower alkyl ester of o-nitrophenyl pyruvic acid in the form of its enolate, i.e. the enol salt or enol ester, with hydrogen peroxide; the enol salt can be the enolate of an alkali metal, an alkaline earth metal or of aluminum, and the enol ester can be the ester formed by the enolic hydroxyl and formic, acetic, propionic or butyric acid.Type: GrantFiled: April 14, 1983Date of Patent: July 31, 1984Assignee: Siegfried AktiengesellschaftInventors: Hans-Rudolf Marti, Rene Gnehm
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Patent number: 4457939Abstract: A series of 5-(2-alkoxy-3-substituted phenyl)hydantoins and pharmaceutically acceptable salts thereof useful as aldose reductase inhibitors and as therapeutic agents for the treatment of chronic diabetic complications; intermediates therefore; and processes for preparation of said compounds.Type: GrantFiled: November 1, 1982Date of Patent: July 3, 1984Assignee: Pfizer Inc.Inventor: Rodney C. Schnur
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Patent number: 4456772Abstract: Optionally substituted fluoro-nitro-benzaldehydes are prepared from optionally substituted halogeno-nitro-benzaldehydes and an alkali metal fluoride in a substantially anhydrous inert aprotic solvent, by heating to 50.degree. to 250.degree. C.Type: GrantFiled: March 3, 1982Date of Patent: June 26, 1984Assignee: Bayer AktiengesellschaftInventors: Gerhard Marzolph, Heinz U. Blank
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Patent number: 4454337Abstract: A new chemical sequence for preparing certain indoles is disclosed which employes certain 2-substituted-6-nitrophenylacetaldehyde semicarbazones claimed here. Said semicarbazones are cyclized to the indoles by low pressure hydrogenation.Type: GrantFiled: March 2, 1983Date of Patent: June 12, 1984Assignee: SmithKline Beckman CorporationInventor: Lawrence I. Kruse
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Patent number: 4450297Abstract: A process for the preparation of o-nitrobenzaldehyde, comprising converting to the corresponding acetals a mixture of nitrated benzaldehyde which contains about 10 to 30% of o-nitrobenzaldehyde and about 70 to 90% of m-nitrobenzaldehyde, removing the o-nitrobenzaldehyde acetal by distillation, and then converting the o-nitrobenzaldehyde acetal to o-nitrobenzaldehyde.Type: GrantFiled: March 17, 1983Date of Patent: May 22, 1984Assignee: Bayer AktiengesellschaftInventors: Michael Preiss, Wolfgang Gau, Horst Behre
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Patent number: 4438269Abstract: The novel compound 4-dimethylaminopyridinium chlorochromate has been found to be an effective oxidizing agent for converting alcohols to their respective aldehydes or ketones, especially for the selective conversion of allylic and benzylic alchols to their corresponding aldehydes and ketones.Type: GrantFiled: August 9, 1982Date of Patent: March 20, 1984Assignee: Thiokol CorporationInventor: Frank S. Guziec, Jr.
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Patent number: 4435601Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.Type: GrantFiled: July 7, 1981Date of Patent: March 6, 1984Assignee: Rhone-Poulenc IndustriesInventors: Karel Formanek, Daniel Michelet, Dominique Petre
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Patent number: 4379765Abstract: There are presented compounds of the formulas ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 and R.sub.3 are selected from the group consisting of hydrogen, lower alkyl, C.sub.2 to C.sub.7 carboxylic acids, hydroxy C.sub.2 to C.sub.7 alkyl, C.sub.2 to C.sub.7 carboxylic acid esters and amides and the group COR.sub.11 wherein R.sub.11 is alkoxy, amino or mono- lower alkyl amino; R.sub.6 is nitro or halo and R.sub.5 is hydrogen or halo,and the pharmaceutically acceptable salts thereof.The pyrazolobenzazepines are useful as anxiolytic and sedative agents.Also provided are processes and intermediates in the production of the above pyrazolobenzazepines.Type: GrantFiled: July 23, 1981Date of Patent: April 12, 1983Assignee: Hoffmann-La Roche Inc.Inventors: George F. Field, Rodney I. Fryer, Eugene J. Trybulski, Armin Walser
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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: 4335055Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4327036Abstract: Process for nuclear chlorination of non-phenolic aromatic compounds, said process comprising contacting and reacting a non-phenolic aromatic compound having a net Hammett .sigma. value of about -0.1 to about 2.0 with chlorine monoxide in the presence of at least one-half an equivalent amount, based on the chlorine monoxide, of an acid having a pK.sub.a no greater than that of trichloroacetic acid, provided, however, when the net Hammett .sigma. value is about 0.7 to about 2.0, the acid has a pK.sub.a no greater than that of trifluoroacetic acid.Type: GrantFiled: May 8, 1980Date of Patent: April 27, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frank D. Marsh
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Patent number: 4316847Abstract: The preparation of racemic and optically pure tryptophans is described. The D-enantiomers of the 6-substituted compounds possess a potent sweetening capability. Novel intermediates are also disclosed.Type: GrantFiled: October 22, 1980Date of Patent: February 23, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Andrew D. Batcho, Urs O. Hengartner, Willy Leimgruber, John W. Scott, Donald Valentine, Jr.
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Patent number: 4306083Abstract: In a two-phase liquid medium comprising an aqueous alkaline solution and an organic solvent, molecular oxygen and a noble metal-containing catalyst can be used to oxidize aryl-substituted alcohols of the formula AR(--CH.dbd.CH--).sub.n CH.sub.2 OH wherein n is 0, 1 or 2, to the corresponding aldehydes. More specifically, the oxidation of an aromatic alcohol, such as p-methoxybenzyl alcohol, can be efficiently carried out in a multiphase system comprising a 5 percent palladium-on-charcoal catalyst, an organic solvent such as methylene chloride, in contact with an aqueous sodium hydroxide solution, in the presence of air or oxygen with good agitation followed by separation of the two phases, recovery of the aldehyde product from the organic solvent and recycle of the aqueous phase without neutralization.Type: GrantFiled: May 15, 1980Date of Patent: December 15, 1981Assignee: The Dow Chemical CompanyInventor: King W. Ma
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Patent number: 4297519Abstract: A process provided for the production of 2-nitrobenzaldehyde from 2-nitrotoluene, in which 2-nitrotoluene is converted, by bromination by a radical mechanism, to 2-nitrobenzyl bromide in the form of a bromination oil containing 20 to 50% or more of 2-nitrobenzyl bromide, and the bromination oil is oxidized directly with a mixture of dimethylsulphoxide and sodium bicarbonate in a weight ratio of 3:1 to 10:1 at temperatures of up to 100.degree. C. and the 2-nitrobenzaldehyde is subsequently isolated via the bisulphite adduct, to give 2-nitrobenzaldehyde in high purity and high yield. The process also has the advantage of a very short reaction time. The 2-nitrobenzaldehyde produced is an important intermediate, for example in the production of pharmaceutically active 1,4-dihydropyridines.Type: GrantFiled: February 28, 1980Date of Patent: October 27, 1981Assignee: Bayer AktiengesellschaftInventor: Werner Ertel
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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: 4213920Abstract: A process for the production of benzaldehydes which are substituted in the ortho-position by an electrophilic group R, which comprises brominating an ortho-substituted compound of the formula I ##STR1## in which R represents the nitro group, the cyano group, an alkoxy group of 1 to 8 carbon atoms or a halogen atom, under irradiation with visible light in an inert solvent, to give the bromide of the formula II ##STR2## converting the resulting bromide by treatment with an alkali bromide in an inert solvent into a styrene compound of the formula III ##STR3## and ozonising this latter compound in an inert solvent to give the compound of the formula IV ##STR4##Type: GrantFiled: June 28, 1978Date of Patent: July 22, 1980Assignee: Ciba-Geigy CorporationInventor: Jacques Gosteli
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Patent number: 4211727Abstract: Carboxylic acid halides are reduced to the corresponding aldehydes using zinc borohydride or cadmium borohydride as the reducing agent.Type: GrantFiled: March 15, 1979Date of Patent: July 8, 1980Assignee: Shell Oil CompanyInventors: Ian D. Entwistle, Robert A. W. Johnstone
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Patent number: 4211726Abstract: There is provided a process for the manufacture of substituted 9,10-anthracenedicarboxaldehydes and substituted 9,10-dihydro-9,10-anthracenedicarboxaldehydes useful as intermediates in the preparation of antibacterial agents.Type: GrantFiled: February 16, 1979Date of Patent: July 8, 1980Assignee: American Cyanamid CompanyInventors: Yang-I Lin, Stanley A. Lang, Jr.
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Patent number: 4206152Abstract: The present invention provides a process for the production of unsubstituted or substituted o-phthalaldehydes by hydrolysis of .alpha.,.alpha., .alpha.',.alpha.'-tetrahalogeno-o-xylenes with a carboxylate in an aqueous medium in the presence of a phase transfer catalyst and an organic base.Type: GrantFiled: December 21, 1978Date of Patent: June 3, 1980Assignee: Ciba-Geigy CorporationInventor: Jacques Gosteli
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Patent number: 4203928Abstract: 2-Nitrobenzaldehyde, a valuable chemical intermediate, is produced by treating the alkali metal salt of a 2-nitrophenylpyruvic acid with an alkali metal hypochlorite in an aqueous medium to produce the corresponding 2-nitrobenzylidene chloride which, upon hydrolysis, yields the desired aldehyde. The 2-nitrophenylpyruvic acid starting material is advantageously prepared through the reaction of a 2-nitrotoluene and a diester of oxalic acid in the presence of an alkali metal alcoholate and can be used directly in the subsequent hypochlorite reaction without isolation. The process is industrially attractive in terms of the overall yield, the availability of starting materials, and the ease of the manipulative steps involved.Type: GrantFiled: March 11, 1975Date of Patent: May 20, 1980Assignee: Bayer AktiengesellschaftInventor: Horst Meyer
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Patent number: T100403Abstract: Hypolipidemic and anti-atherosclerotic 2- or 3-(monosubstituted-amino) phenyl compounds of the formulae: ##STR1## wherein R.sub.1 is a saturated or unsaturated hydrocarbon radical of 8-19 carbon atoms which may be branched or unbranched and which may contain one or more radicals selected from the group consisting of saturated or unsaturated cycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; J is ##STR2## wherein Z is inter alia hydrogen, loweralkyl, hydroxy, loweralkoxy and loweralkoxyalkoxy, or J is carboxyloweralkyl, carboxyloweralkenyl, carboxyloweralkynyl, carboalkoxyloweralkyl, carboalkoxyloweralkenyl or carboalkoxyloweralkynyl.Type: GrantFiled: October 17, 1979Date of Patent: March 3, 1981Assignee: American Cyanamid CompanyInventor: Robert G. Shepherd