Aromatic Alcohol Moiety Patents (Class 560/254)
-
Patent number: 4310465Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: December 17, 1979Date of Patent: January 12, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Gabriel Saucy
-
Patent number: 4310688Abstract: The level of hydrolyzable chloride-containing impurities in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by reacting the impurities with a vicinal epoxide-containing compound and then fractionally distilling the mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) in a methylene chloride solution containing 0.084 weight percent of hydrolyzable chloride is contacted with a diglycidyl ether of bisphenol A at 23.degree. C. This reaction mixture is then fractionally distilled to separate the IEM from the methylene chloride first cut and the epoxy resin residue. The hydrolyzable chloride level of the distilled IEM product is only 0.03 weight percent.Type: GrantFiled: October 22, 1979Date of Patent: January 12, 1982Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
-
Patent number: 4308400Abstract: Aromatic-aliphatic ketones of the formulae I, II, III or IV ##STR1## wherein n is 1 or 2, Ar is an aryl radical, R.sup.1 and R.sup.2 are monvalent aliphatic, cycloaliphatic or araliphatic radicals, R.sup.3 is a direct bond or a divalent organic radical, X is a hydroxyl or amino group or the monovalent etherification or silylation products thereof, and X' is a divalent amino, ether or silyloxy group, Y is a direct bond or CH.sub.2 and Z is O, S, SO.sub.2, CH.sub.2 or C(CH.sub.3).sub.2, are suitable sensitizers for the photopolymerization of unsaturated compounds and for the photochemical crosslinking of polyolefins. Some of these compounds are novel and can be obtained by methods analogous to those for obtaining the known compounds of this type.Type: GrantFiled: December 28, 1979Date of Patent: December 29, 1981Assignee: Ciba-Geigy A.G.Inventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Husler
-
Patent number: 4306097Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 8, 1980Date of Patent: December 15, 1981Assignee: Pfizer Inc.Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4291176Abstract: Insecticidally active vinyl-cyclopropane carboxylic acid esters of the formula ##STR1## are prepared by reacting ##STR2## in which R.sup.12 is a radical selected from the group consisting of ##STR3## with an alcoholate of the formulaM--O--R.sup.8.Various processes for making the intermediates are also described. Many of the intermediates and end products are new.Type: GrantFiled: August 24, 1977Date of Patent: September 22, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Heine, Willy Hartmann
-
Patent number: 4283569Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 -C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.Type: GrantFiled: September 13, 1977Date of Patent: August 11, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
-
Patent number: 4276430Abstract: Dihydroxybenzoic acid derivatives and compositions containing same are useful for topical application to the skin as well as for systemic administration. The compounds are especially effective for providing an analgesic, anti-pyretic, and anti-inflammatory effect.Type: GrantFiled: July 26, 1979Date of Patent: June 30, 1981Assignee: The Procter & Gamble CompanyInventors: Herbert H. Reller, Herbert C. Kretschmar
-
Patent number: 4275201Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester.Type: GrantFiled: February 14, 1979Date of Patent: June 23, 1981Assignee: Sterling Drug Inc.Inventor: Joseph C. Collins
-
Patent number: 4273943Abstract: Methylvanillyl ketone is prepared from a "through process" involving oxidation of isoeugenol followed by subsequent acidic hydrolysis.Type: GrantFiled: September 28, 1979Date of Patent: June 16, 1981Assignee: Merck & Co., Inc.Inventors: George Gal, Seemon H. Pines
-
Patent number: 4268688Abstract: This invention relates to a process for the preparation of optically active aldehydes by the asymmetric catalytic hydroformylation of olefins. The process comprises the hydroformylation of olefinically unsaturated prochiral compounds in the presence of an optically active coordination compound containing a metal which is selected from the group consisting of rhodium, iridium, and cobalt.This invention describes a generalized process for the asymmetric hydroformylation of a wide variety of olefins in which a preponderance of one optical isomer is produced. It is especially useful for the preparation of natural products which may require the presence of only one optical isomer for their utilization, for example, as flavors, fragrances, and medications.The catalyst systems for the process of this invention are formed in the presence of carbon monoxide and hydrogen, from coordination compounds consisting of a central metal atom, rhodium, iridium, or cobalt, and at least one optically active ligand, e.g.Type: GrantFiled: February 16, 1973Date of Patent: May 19, 1981Assignee: Monsanto CompanyInventors: Harold B. Tinker, Arthur J. Solodar
-
Patent number: 4229366Abstract: The invention relates to a process for nucleophilic substitution reactions. According to the invention the reaction is carried out in a heterogeneous system, consisting of a solid and a dissolved reactant, one or several organic solvents, one or several linear polyether derivatives, and/or amino compounds and water.The volume of the water is preferably at the most 100% of the volume of the organic solvent and more preferably 5%.According to the invention the anhydrous reaction medium which is difficult to ensure, is not necessary and the use of the expensive and in industrial scales unavailable crown ethers is eliminated.Type: GrantFiled: October 20, 1978Date of Patent: October 21, 1980Assignee: Chinoin Gyogyszer es Vegyeszeti Termeker Gyara Rt.Inventors: Laszlo Toke, Gabor T. Szabo, Gabor Szabo, Lajos Nagy, Istvan Rusznak
-
Patent number: 4225619Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is perfluoroalkyl of 1 to 8 carbon atoms or 2,2,3,3-tetrafluoro-cyclobutyl,R.sub.2 and R.sub.4, which may be identical to or different from each other, are each hydrogen, alkyl of 1 to 10 carbon atoms, aliphatic acyl of 2 to 18 carbon atoms, benzoyl, salicyloyl or phenylacetyl, andR.sub.3 and R.sub.5, which may be identical to or different from each other, are each alkyl of 3 to 18 carbon atoms, halogen, nitro, p-toluenesulfonyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclododecyl, methylcyclohexyl, dimethylcyclohexyl, benzyl, methylthio or ##STR2## where R.sub.1, R.sub.2 and R.sub.4 have the meanings previously defined,Q is --CH.sub.2 -- or --S--, andG is R.sub.5, as above defined, orQ is R.sub.3, as above defined, andG is --CH.sub.2 -- or --S--,R.sub.3 may, in addition, also be hydroxyl, methoxy, methyl or cyano, andR.sub.5 may also be methyl, orone of substituents R.sub.3 and R.sub.Type: GrantFiled: March 19, 1979Date of Patent: September 30, 1980Assignee: Boehringer Ingelheim GmBHInventors: Rolf Brickl, Hans Eberhardt, Karl-Richard Appel, Uwe Lechner, Walter Merk
-
Patent number: 4223160Abstract: Niobium and ruthenium salts are employed as catalyst in the reaction of oxirane compounds with carboxylic acids. The acrylate esters produced can be used in photocurable compositions.Type: GrantFiled: March 26, 1979Date of Patent: September 16, 1980Assignee: Union Carbide CorporationInventor: Lawrence G. Hess
-
Patent number: 4219667Abstract: Sulphones of the formula:RSO.sub.2 CH.sub.2 CX.dbd.CYCH.sub.2 OR.sub.1where R is alkyl, aralkyl, alkylaryl or aryl, R.sub.1 is hydrogen or -COR.sub.2 where R.sub.2 is hydrogen, alkyl or aryl, and one of X and Y is methyl and the other is hydrogen are useful for converting terpene and carotenoid compounds into the immediately higher isoprenologue, useful as perfumes, foodstuff dyes, and pharmaceuticals.Type: GrantFiled: December 5, 1973Date of Patent: August 26, 1980Assignee: Rhone-Poulenc S.A.Inventors: Marc Julia, Albert Menet
-
Patent number: 4217394Abstract: There are disclosed mold-release compositions suitable for lubricating metal molds which are used in molding natural and synthetic rubber and other polymers. The mold release agents of the invention are oxidation-stable homopolymer and copolymer, i.e., block or heteric polyoxyalkylene lubricant compounds. The lubricants of the invention can be used alone or in mixtures with prior art polyoxyalkylene lubricant compounds. The polyoxyalkylene mold release lubricants of the invention have the formula: ##STR1## R is individually selected from alkyl groups of 1 to about 21 carbon atoms, preferably about 7 to about 21 carbon atoms, and most preferably about 12 to about 18 carbon atoms. In lubricants I and III, R.sub.1 and R.sub.2 are the residue of the same or different and in lubricant II different alkylene units, all individually selected from the group consisting of the residue of ethylene oxide, propylene oxide, butylene oxide and an aromatic glycidyl ether, R.sub.3 is the residue of a difunctional phenol, R.Type: GrantFiled: December 26, 1978Date of Patent: August 12, 1980Assignee: BASF Wyandotte CorporationInventors: David D. Newkirk, Robert B. Login, Basil Thir
-
Patent number: 4215215Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.Type: GrantFiled: July 6, 1979Date of Patent: July 29, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
-
Patent number: 4208333Abstract: Preparation of chroman-2-acetic acid from 2-hydroxy-chromanes or derivatives thereof and intermediates in this synthesis.Type: GrantFiled: December 15, 1978Date of Patent: June 17, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Noal Cohen
-
Patent number: 4206310Abstract: An improved process for producing an ester from a carboxylic acid and an alcohol which comprises reacting said carboxylic acid with said alcohol by the use of a 1-substituted-2-halopyridinium salt or a 1-substituted-2-haloquinolinium salt as a condensing agent in the presence of a hydrogen halide captor. According to this process, various esters, even if they have some steric hindrances, may be obtained in good yields.Type: GrantFiled: September 8, 1978Date of Patent: June 3, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Masahiro Usui, Kazuhiko Saigo, Eiichiro Shimada
-
Patent number: 4202978Abstract: There are disclosed compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR2## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy, and ##STR3## wherein R.sub.1 is selected from the group consisting of lower alkyl; R.sub.8 is selected from the group consisting of --O--(CH.sub.2).sub.n --wherein n is 2 to 20, ##STR4## and R.sub.6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products.The end products have utility as agents exhibiting both .alpha. and selective .beta. adrenergic blocking action.Type: GrantFiled: February 8, 1978Date of Patent: May 13, 1980Assignee: Hoffmann-La Roche Inc.Inventors: Kenneth E. Fahrenholtz, Robert W. Guthrie, Richard W. Kierstead, Jefferson W. Tilley
-
Patent number: 4201864Abstract: Compounds of formula (I): ##STR1## wherein: m is 1 or 2; n is 4 to 8; X is CO, protected CO, or CROH wherein R is hydrogen or C.sub.1-4 alkyl and wherein the OH moiety may be protected; R.sub.1 is hydrogen or CO.sub.2 R.sub.1 represents an ester group in which the R.sub.1 moiety contains from 1 to 12 carbon atoms; R.sub.3 is hydroxy, or protected hydroxy; R.sub.2 and R.sub.4 are separately hydrogen, C.sub.1-9 alkyl, C.sub.5-8 cycloalkyl, C.sub.5-8 cycloalkyl-C.sub.1-6 alkyl, phenyl, phenyl C.sub.1-6 alkyl, naphthyl, naphthyl C.sub.1-6 alkyl, any of which phenyl or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or nitro groups; or R.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and salts thereof; except that when one of R.sub.2 and R.sub.4 is hydrogen or C.sub.1-4 alkyl then the other of R.sub.2 and R.sub.4 cannot be hydrogen or C.sub.Type: GrantFiled: November 22, 1978Date of Patent: May 6, 1980Assignee: Beecham Group LimitedInventors: Frederick Cassidy, Gordon Wootton
-
Patent number: 4173574Abstract: Phenolic age resistors such as 4-(3,5-ditertiary butyl-4-hydroxyphenyl)-2-butyl 2-methyl-4-thia-6-octanoyloxyhexanoate are used as antioxidants in diene rubbers, such as butadiene-styrene types and in polyolefins, such as polypropylene.Type: GrantFiled: October 11, 1977Date of Patent: November 6, 1979Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline
-
Patent number: 4169100Abstract: Compounds represented by the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are lower alkyl, R.sub.4 is lower alkoxy, R.sub.6 and R.sub.8 are methyl or trifluoro methyl, R.sub.9 is formyl, hydroxymethyl, alkoxymethyl, alkanoyloxymethyl, carboxyl, alkoxycarbonyl, lower alkenoxycarbonyl, lower alkynoxycarbonyl, carbamoyl, mono(lower alkyl)-carbamoyl, di(lower alkyl)carbamoyl or N-heterocyclylcarbonyl, R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 and R.sub.13 are hydrogen or fluorine with the proviso that at least one of R.sub.5, R.sub.7, R.sub.10, R.sub.11, R.sub.12 or R.sub.13 is fluorine or at least one of R.sub.6 or R.sub.8 is trifluoro methyl, or pharmaceutically acceptable salts thereof useful as antitumor agents are disclosed.Type: GrantFiled: October 18, 1978Date of Patent: September 25, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, Beverly A. Pawson
-
Patent number: 4164510Abstract: Isopropylphenyl esters are converted to di- or trihydric phenols via a novel autoxidation of the esters at high conversion rates to the corresponding hydroperoxyisopropylphenyl esters in the presence of a catalyst combination comprising at least two members selected from the group consisting of (i) a metal phthalocyanine; (ii) a di-tertiary alkyl peroxide; and (iii) a tertiary alkyl hydroperoxide.Rearrangement of the hydroperoxyisopropylphenyl esters to the corresponding hydroxyphenyl esters and the hydrolysis of the latter compounds provides the phenols in overall yields (from the starting esters) heretofore not obtainable. Novel bis(hydroperoxyisopropylphenyl)carbonates are described which are attractive intermediates for the intermediate bisphenol carbonate or the final hydroquinone hydrolysis product.Type: GrantFiled: February 21, 1978Date of Patent: August 14, 1979Assignee: The Upjohn CompanyInventor: Sheng-Hong A. Dai
-
Patent number: 4163103Abstract: Novel 9-substituted phenyl-3,7-dimethyl-nona-2,4,6,8-tetraene derivatives useful as anti-tumor agents.Type: GrantFiled: May 8, 1978Date of Patent: July 31, 1979Assignee: Hoffmann-La Roche Inc.Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
-
Patent number: 4160035Abstract: A plant protecting composition with pesticidal effects contains an effective amount of at least one compound of the formula ##STR1## wherein R is a C.sub.1-20 alkyl group or a phenyl or phenyl-C.sub.1-3 alkylene group having optionally one or more C.sub.1-3 alkyl or halogen substituents on the phenyl ring, and a diluent in an amount necessary to make up the final weight of the composition. To kill plant pests, the composition is applied to growing plants either prior to or after emergence.Type: GrantFiled: November 3, 1977Date of Patent: July 3, 1979Assignee: Egyt Gyogyszervegyeszeti GyarInventors: Laszlo Levai, Gyula Mikite, Attila Kis-Tamas
-
Patent number: 4159991Abstract: .alpha.-Acyloxy-N,N'-diacylmalonamides of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, straight chain or branched alkyl radicals having from one to eleven carbon atoms, or hydrocarbon radicals with six to twelve carbon atoms and comprising at least one aromatic ring, are novel compounds prepared by the action of a mixture of carboxylic acids R.sub.3 COOH and R.sub.4 COOH upon an .alpha.-acyloxymalononitrile, R.sub.1 COO--C(CN).sub.2 --R.sub.2, in the presence of an acid catalyst and are useful as intermediates in organic synthesis and low temperature activators in bleaching or scouring compositions.Type: GrantFiled: August 22, 1977Date of Patent: July 3, 1979Assignee: Produits Chimiques Ugine KuhlmannInventors: Bernard Dubreux, Serve Y. Delavarenne, Jean-Pierre Schirmann
-
Patent number: 4154842Abstract: 1-Azolyl-4-hydroxy-1-phenoxy-butane derivatives of the formula ##STR1## in which R is hydrogen, --CO--R.sup.1 or --SO.sub.2 --R.sup.2,R.sup.1 is cycloalkyl, alkylamino, dialkylamino, alkenyl, alkynyl, or optionally substituted alkyl, phenyl, phenoxyalkyl, phenylalkyl or phenylamino,R.sup.2 is alkyl or optionally substituted phenyl,A is --CO--or CH(OH),X is H or --OR,X.sup.1 is alkyl or optionally substituted phenyl,Y is CH or N,Z is halogen, alkyl, halogenoalkyl, cycloalkyl, alkoxy, alkylthio, alkoxycarbonyl, amino, cyano, nitro, or optionally substituted phenyl, phenoxy or phenylalkyl, andN is 0, 1, 2, 3, 4 or 5,Or a salt thereof, which possess fungicidal and bactericidal properties.Type: GrantFiled: July 27, 1977Date of Patent: May 15, 1979Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kramer, Karl H. Buchel, Paul-Ernst Frohberger, Peter Kraus
-
Patent number: 4150235Abstract: Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.Type: GrantFiled: December 17, 1976Date of Patent: April 17, 1979Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking
-
Patent number: 4148696Abstract: The electrochemical oxidation of activated alkyl substituted aromatic compounds in which the alkyl substituent is acyloxylated in a direct oxidation process may be effected by treating an activated alkyl substituted aromatic compound with a fatty acid, an alkali metal or alkaline earth metal salt thereof and a phase transfer agent in an electrochemical cell to form oxidative products of the starting compound.Type: GrantFiled: March 20, 1978Date of Patent: April 10, 1979Assignee: UOP Inc.Inventor: Mark A. Halter
-
Patent number: 4147708Abstract: A novel procedure for the preparation of carotenoids, particularly vitamin A, employing .pi.-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.Type: GrantFiled: May 2, 1977Date of Patent: April 3, 1979Assignee: Hoffmann-La Roche Inc.Inventor: Percy S. Manchand
-
Patent number: 4145362Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.Type: GrantFiled: May 10, 1977Date of Patent: March 20, 1979Assignee: S.A. P R B en Neerlandais PRB N.V.Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
-
Patent number: 4140789Abstract: A compound of the formula ##STR1## in which R.sub.1 denotes optionally substituted lower akyl which is optionally branched at the linking carbon atom, R.sub.2 represents hydrogen or lower alkanoyl and R.sub.3 is a group of the formula --R.sub.3.sup.a -(R.sub.3.sup.b).sub.n -- (Ia), in which R.sub.3.sup.1 represents the radical of the formula --N(R.sub.4)-- or --O-- and R.sub.4 represents hydrogen or lower alkyl, R.sub.3.sup.b denotes the radical of the formula --CH.sub.2 -- or, if R.sub.3.sup.a represents --N(R.sub.4)--, denotes the radical of the formula --C(.dbd.O)-- and n represents nought or 1, and a group of the formula Ia, in which n represents 1, can be linked to the carbonyl group of the carbamoyl grouping either via the group R.sub.3.sup.a or the group R.sub.3.sup.b, or acid addition salts thereof, which can be used pharmaceutically can be used as beta-receptor blocking agents for the treatment of disorders in the cardiac rhythm and coronary heart diseases.Type: GrantFiled: December 16, 1976Date of Patent: February 20, 1979Assignee: Ciba-Geigy CorporationInventors: Knut A. Jaeggi, Franz Ostermayer, Herbert Schroter
-
Patent number: 4140861Abstract: Novel interphenylene derivatives of 11,12-secoprostaglandins are prepared by the stepwise alkylation of the ethyl ester or the t-butyl ester of acetoacetic acid. One such method involves treatment of the t-butyl ester of acetoacetic acid with a strong base to form the anion followed by treatment with ethyl p-(3-bromopropyl)benzoate to produce ethyl 4-(4-tert-butoxycarbonyl-5-oxo-hexyl)benzoate, subsequently reacting the anion of the thus-formed benzoate with 1-chloro-4-acetoxynonane to produce ethyl 4-(4-acetyl-4-tert-butoxycarbonyl-8-acetoxytridecyl)benzoate followed by decarboxylation and alkaline hydrolysis to produce the desired product 4-(4-acetyl-8-hydroxytridecyl)benzoic acid which is useful as a pharmaceutical in the treatment of patients with renal failure and in the prevention of transplant rejection.Type: GrantFiled: May 18, 1978Date of Patent: February 20, 1979Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., John B. Bicking
-
Patent number: 4140725Abstract: Compounds of the formula: ##STR1## are disclosed which compound are used to prepare carbamates which are stated to have utility as plant protecting agents and insecticides.Type: GrantFiled: August 29, 1977Date of Patent: February 20, 1979Assignee: BASF AktiengesellschaftInventors: Karl Kiehs, Rolf Huber
-
Patent number: 4132702Abstract: Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another denote alkyl, cycloalkyl or aralkyl, R.sub.3 denotes hydrogen or, conjointly with R.sub.1, denotes tetramethylene, R.sub.4 denotes hydrogen or lower alkyl or, conjointly with R.sub.2, denotes tetramethylene, R.sub.5 denotes hydrogen, alkyl, aralkyl, acyloxyalkyl, oxaalkyl or phenyl, R.sub.6 denotes hydrogen, alkhyl, phenyl or the group or, conjointly with R.sub.5, denotes alkylene, R.sub.7 denotes hydrogen, alkyl, phenyl, benzyl or alkylphenyl or, conjointly with R.sub.5 or R.sub.6, denotes alkylene or, conjointly with R.sub.5 and R.sub.6, denotes alkanetriyl, R.sub.5, R.sub.6 and R.sub.7 together containing at least one carbon atom, Y denotes --O-- or --NH--, P denotes 1, 2, 3 or 4 and A denotes hydrogen or a group which is derived from an organic or inorganic oxygen acid A-(OH).sub.p, are suitable for stabilizing organic material against thermo-oxidative degradation.Type: GrantFiled: July 27, 1976Date of Patent: January 2, 1979Assignee: Ciba-Geigy CorporationInventors: Andreas Schmidt, Kurt Schwarzenbach
-
Patent number: 4127728Abstract: A process for the preparation of a substituted 1-phenyl-2,2,2-trihalo-ethanol ester of the formula ##STR1## in which R is alkyl, halogenoalkyl, alkoxy, cycloalkyl or optionally substituted phenyl, benzyl, phenoxy, or phenylsulfonyl,X is halogenoalkyl with 1-3 carbon atoms and 1-3 halogen atoms,Y is halogen, cyano, nitro, alkyl, alkoxy, alkylmercapto, sulfoalkoxy or optionally substituted methylenedioxy, andn is an integer from 0 to 3,Comprising reacting a compound of the formula ##STR2## WITH A HALOGENATED ALDEHYDE OF THE FORMULAX CHOin the presence of a Friedel-Crafts catalyst at a temperature of about -70 to +100.degree. C thereby to form a complex alcoholate, and reacting the complex alcoholate with an acid halide of the formula ##STR3## OR WITH A CORRESPONDING ACID ANHYDRIDE AT A TEMPERATURE OF ABOUT -70 TO +100.degree. C.Type: GrantFiled: August 24, 1976Date of Patent: November 28, 1978Assignee: Bayer AktiengesellschaftInventors: Thomas Schmidt, Wolfgang Kramer, Eckart Kranz
-
Patent number: 4125735Abstract: A process for the synthesis of perfume products, Vitamin E and intermediates described herein involving a coupling reaction. For instance, a process for the synthesis of dehydrophytol and Vitamin E comprising forming a C.sub.15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C.sub.20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.Type: GrantFiled: October 16, 1975Date of Patent: November 14, 1978Assignee: SCM CorporationInventors: Ralph E. Close, William Oroshnik
-
Patent number: 4123614Abstract: The present invention relates to novel assay reagents, their composition, methods of preparation, and use in the detection and measurement of various biological systems and/or components, e.g. enzymes, antibodies, antigens, and periodate concentration. This invention in its basic form utilizes a class of compounds having, inter alia., a backbone chain, an indicator group, and vicinal oxidizable groups.Type: GrantFiled: October 18, 1976Date of Patent: October 31, 1978Assignee: Syntex (U.S.A.) Inc.Inventor: David H. Rammler
-
Patent number: 4123552Abstract: Fungus and mold growth in crops and organic matter are inhibited by the use of bis-carboxylic acid esters and compositions thereof. In a preferred embodiment, crops and animal feedstuffs are preserved during storage by applying a microbiocidal amount of a mono-, di or trioxymethylene, or lower alkylidene bis-alkanoate, or a mixture thereof.Type: GrantFiled: October 17, 1975Date of Patent: October 31, 1978Assignee: Chevron Research CompanyInventors: Daniel L. Kensler, Jr., Gustave K. Kohn, David D. Walgenbach
-
Patent number: 4112228Abstract: 7-(D-.alpha.-Hydroxy-2-arylacetamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triaz olo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids and derivatives containing blocking groups on the .alpha.-hydroxy group and their nontoxic, pharmaceutically acceptable salts are valuable as antibacterial agents and are particularly valuable as therapeutic agents in poultry and in animals, including man, in the treatment of infectious diseases caused by many Gram-positive and Gram-negative bacteria. A preferred compound is 7-(D-mandelamido)-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin -3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acid.Type: GrantFiled: March 16, 1977Date of Patent: September 5, 1978Assignee: Bristol-Myers CompanyInventors: Takayuki Naito, Jun Okumura, Hajime Kamachi
-
Patent number: 4110227Abstract: Lubricants for synthetic fibers such as polyester and nylon are disclosed which are improved oxidation stable polyoxyalkylene lubricant compounds. Such lubricant compounds can be used alone as textile fiber lubricants or in combination with other polyoxyalkylene compounds useful as fiber lubricants but which are subject to oxidative degradation under conditions of heating at temperatures at least above 200.degree. C. An improved textile fiber is produced by the use of such fiber lubricants in conventional processes for producing continuous filament, false twist, textured yarn as well as other type yarns.The improved oxidation stable homopolymer and copolymer, i.e.Type: GrantFiled: September 19, 1977Date of Patent: August 29, 1978Assignee: BASF Wyandotte CorporationInventors: David Dudley Newkirk, Robert Bernard Login, Basil Thir
-
Patent number: 4094797Abstract: There are disclosed oxidation stable heteric or block copolymer polyoxyalkylene compositions suitable for the treatment of thermoplastic fibers, particularly polyester and nylon fibers, prior to the processing of such fibers in conventional processes to impart false twist, or to produce textured yarn or other type yarns by mechanical heat treatment and tensioning processes. The polyoxyalkylene compounds of the invention derived from lower alkylene oxides can be initiated with a difunctional aromatic compound containing reactive hydrogens such as a dihydroxyphenol to obtain an aromatic nucleus in the polymer chain and are capped on at least one end of the chain with an alpha-olefine epoxide or mixtures thereof with at least one aliphatic monocarboxylic acid. Hydroxyl functionality can be retained on one end of the molecule.Type: GrantFiled: August 1, 1977Date of Patent: June 13, 1978Assignee: BASF Wyandotte CorporationInventors: David Dudley Newkirk, Robert Bernard Login, Basil Thir
-
Patent number: 4091225Abstract: This invention comprises an alkylation, reduction and transesterification process for the preparation of ester substituted phenols. The products are useful as antioxidants and may be prepared in high yields and with a high degree of purity.Type: GrantFiled: January 22, 1974Date of Patent: May 23, 1978Assignee: The Goodyear Tire & Rubber CompanyInventor: Dane K. Parker
-
Patent number: 4087435Abstract: Novel 8-aza-9-dioxothiaprostanoic acid compounds, their salts, and derivatives, are prepared from ethyl 7-(3-hydroxymethyl-2-isothiazolidinyl)-5-heptynoate S,S-dioxide by first hydrogenating the triple bond over a Lindlar catalyst, followed by mild oxidation, to produce the corresponding 3-formyl compound, which is condensed with the ylide prepared from dimethyl-(2-oxoheptyl)phosphonate to produce the .alpha.,.beta.-unsaturated ketone, followed by reduction to the corresponding carbinol, and ester hydrolysis. The compounds are useful especially for the treatment of patients with poorly functioning kidneys, as hypotensives, or as platelet aggregation inhibitors.Type: GrantFiled: February 17, 1977Date of Patent: May 2, 1978Assignee: Merck & Co., Inc.Inventors: Edward J. Cragoe, Jr., James H. Jones, John B. Bicking
-
Patent number: 4081476Abstract: The compounds are 1-aryl-1-lower alkyl-substituted-1-buten-3-ols, butan-3-ols, and acylation products thereof, e.g., (p-biphenylyl)-2-penten-4-ol and are useful as pharmaceuticals.Type: GrantFiled: November 19, 1975Date of Patent: March 28, 1978Assignee: Sandoz, Inc.Inventors: Paul L. Anderson, Darryl A. Brittain
-
Patent number: 4069385Abstract: In the preparation of olefin derivatives having an ester group at the allylic position (hereinafter referred to as "allylic ester(s)") which comprises reacting an olefin having at least one hydrogen atom at the allylic position and which will produce an allylic ester having an asymmetric carbon atom with an organic peroxide in the presence of a copper catalyst, a method for producing optically active allylic esters characterized by using, as the copper catalyst, an optically active copper complex derived from an optically active compound selected from the group consisting of Schiff's bases of the formula: ##STR1## and amino acids of the formula: ##STR2## wherein R.sub.0 is an optically active alkyl, cycloalkyl, aralkyl or aryl group which may contain an unsaturated bond and/or a substituent having a hetero atom, X and Y are each a hydrogen atom, an alkyl, cycloalkyl, aralkyl or aryl group, or a substituent having a hetero atom, R.sub.1 and R.sub.Type: GrantFiled: June 3, 1976Date of Patent: January 17, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Araki, Tsuneyuki Nagase
-
Patent number: 4060544Abstract: A phenyl amino compound having a tertiary amino group contain one or two N-bonded --C.sub.2 H.sub.4 CONHC(CH.sub.3).sub.2 CH.sub.2 COCH.sub.3 moieties; said tertiary amino group being bonded through the nitrogen atom to the phenyl group. These compounds are suitable for use as coupling agents in the preparation of keto-amido containing aminophenyl-azo dyestuffs.Type: GrantFiled: August 18, 1975Date of Patent: November 29, 1977Assignee: GAF CorporationInventors: Lester N. Stanley, Russell E. Farris
-
Patent number: 4058569Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: March 1, 1976Date of Patent: November 15, 1977Assignee: SCM CorporationInventor: William Oroshnik