Carboxyl, Or Salt Thereof, Not Bonded Directly To Ring Patents (Class 562/496)
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Patent number: 4927967Abstract: A process for the production of organic carboxylic acids by the catalytic reaction of organic formate esters in contact with carbon monoxide and a homogeneous catalyst system of rhodium metal atom, a phosphorus containing ligand in which there is present at least one oxo oxygen atom attached to a phosphorus atom or a carbon atom to form a Z group and the ##STR1## group in said Z group is located at least one carbon atom removed and preferably from 2-4 carbon atoms removed from the phosphorus atom of the molecules represented by the formulas ##STR2## and a halogen source, under mild reaction conditions, wherein R' is H, aryl, alkaryl, aralkyl or alkyl, and wherein 1 or more of said R' groups can be substituted with a Z group but not more than 3 of said R' groups in the molecule are so substituted; a is an integer from 0-4; b is an integer from 0-3; and Z is P(O)R'R'; --C(O)OR" or C(O)R", wherein R" is R'.Type: GrantFiled: November 6, 1985Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Richard W. Wegman
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Patent number: 4922009Abstract: A stereoconvergent process is described for preparing optically active alpha-arylalkanoic acids using as starting substance a diastereoisomeric mixture of ketals of formula ##STR1## in which the substituents have the meanings given in the description. The described process leads to the formation of a single enantiomer.Type: GrantFiled: December 23, 1987Date of Patent: May 1, 1990Assignee: Zambon SpAInventors: Marco Villa, Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli
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Patent number: 4918226Abstract: A process for converting formic acid esters or transesterification products thereof to carboxylic acids comprising contacting a formic acid ester of the formula (HCOO).sub.n --R where R is aliphatic, cycloaliphatic or aralkyl and n is 1 or 2 with a catalytically effective amount of a soluble iridium salt and an iodide promoter at a temperature of from about 100.degree. C. to about 300.degree. C. in the presence of an organic solvent containing at least one carboxylic acid.Type: GrantFiled: June 22, 1981Date of Patent: April 17, 1990Assignee: Exxon Research and Engineering CompanyInventor: Roy L. Pruett
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Patent number: 4910337Abstract: .alpha.-Arylalkanoic acids are prepared by a method comprising the step of reacting an alkylaromatic compound corresponding to the desired .alpha.-arylalkanoic acid with a new metallation reagent solution. The reagent comprises the reaction product of alkyllithium or aryllithium and about two to five molar equivalents of potassium tert-alkoxide in a trialkylamine solvent.Type: GrantFiled: January 27, 1989Date of Patent: March 20, 1990Assignee: Mine Safety Appliances CompanyInventors: Kuen-Wai Chiu, Mary H. Staruch, David H. Ellenberger
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4883916Abstract: A polyprenyl compound terminated with a group of ##STR1## is novel and useful as an antihypercholesterolemic agent and an antiarteriosclerotic agent, in which X is a group of the formula ##STR2## wherein K and L are independently a hydrogen atom or form a single valence bond between the carbon atoms to which they are attached, a group represented by the formula --CH.sub.2 -- or a group represented by the formula --(CH.sub.2).sub.2 --, m is an integer of 0 or 1, and R stands for a hydroxy group, a group represented by the Formula ##STR3## wherein R.sup.1 and R.sup.2 may be the same or different and each stands for a hydrogen atom or a lower alkyl group and p stands for an integer of 1 or 2, a group represented by the formula --NH--(CH.sub.2).sub.Type: GrantFiled: April 1, 1988Date of Patent: November 28, 1989Assignee: Eisai Co., Ltd.Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
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Patent number: 4864038Abstract: Novel 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors which are useful as antihypercholesterolemic agents and are represented by the following general structural formulae (I) and (II): ##STR1## and pharmaceutically acceptable salts of the compounds (II) in which Z is hydrogen are disclosed.Type: GrantFiled: June 10, 1988Date of Patent: September 5, 1989Assignee: Merck & Co., Inc.Inventors: William F. Hoffman, Ta J. Lee, Clarence S. Rooney
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Patent number: 4822913Abstract: Esters of carboxylic acids of the formula RCH.sub.2 COOR"' and R'CH:C(R")COOR"' are reacted to form a carboxylic acid and an aliphatic alcohol R"'OH wherein R, R', and R" are individually selected from the group consisting of --H, alkyl moieties of from 1 to 18 carbon atoms and aralkyl moieties, cycloalkyl moieties and alkylaryl moieties of 3 to 18 carbon atoms and R"' is an alkyl moiety of 1 to 18 carbon atoms in the presence of an AMS-1B borosilicate crystalline molecular sieve catalyst under reaction conditions.Type: GrantFiled: October 28, 1983Date of Patent: April 18, 1989Assignee: Amoco CorporationInventor: Gary P. Hagen
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Patent number: 4801719Abstract: Compounds of the formula Ia ##STR1## in which X and R.sup.1 to R.sup.6 are as defined in the claims, are obtainable by reacting monochlorosilanes of the formula II ##STR2## with tetrasubstituted ethylenes of the formula III ##STR3## X as Cl and Br can be replaced by ester groups of inorganic and organic acids. The compounds of the formula I and those with other ester groups are suitable especially as a protective-group reagent for hydroxyl, mercapto, carboxyl, amino and amide groups.Type: GrantFiled: June 8, 1987Date of Patent: January 31, 1989Assignee: Ciba-Geigy CorporationInventors: Konrad Oertle, Hansjurg Wetter
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Patent number: 4788330Abstract: A polyprenyl compound terminated with a group of ##STR1## is novel and useful as an antihypercholesterolemic agent and an antiarteriosclerotic agent, in which X is a group of the formula ##STR2## (wherein K and L are independently a hydrogen atom or form a single valence bond between the carbon atoms to which they are attached), a group represented by the formula --CH.sub.2 -- or a group represented by the formula --(CH.sub.2).sub.2 --, m is an integer of 0 or 1, and R stands for a hydroxy group, a group represented by the formula ##STR3## wherein R.sup.1 and R.sup.2 may be the same or different and each stands for a hydrogen atom or a lower alkyl group and p stands for an integer of 1 or 2, a group represented by the formula --NH--(CH.sub.2).sub.Type: GrantFiled: March 7, 1986Date of Patent: November 29, 1988Assignee: Eisai Co., Ltd.Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
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Patent number: 4786744Abstract: The invention relates to a method for opening the ring of gem dicyanepoxides comprising reacting a gem dicyanepoxide with a mononucleophilic compound in the presence of a hydrohalic acid or a weakly nucleophilic acid.Type: GrantFiled: June 17, 1985Date of Patent: November 22, 1988Assignee: Centre National de la Recherche ScientifiqueInventors: Albert L. F. Robert, Jean-Luc Guinamant, Sylvie C. A. Jaguelin
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Patent number: 4762948Abstract: An optically active arylacetic acid derivative of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are the same or different and are each an hydrogen atom, a lower alkyl group or a phenyl group; and Ar is a group of the formula: ##STR2## a group of the formula: ##STR3## wherein R.sub.3 and R.sub.4 are the same or different and are each a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a difluoromethoxy group, a trifluoromethyl group or a phenyl group is prepared in good conversion and optical yield by asymmetrically reducing an ethylenically unsaturated compound of the formula: ##STR4## wherein R.sub.1, and R.sub.2 and Ar are the same as defined above with hydrogen in the presence of a metal catalyst modified with a ligand selected from the group consisting of a specific optically active metallocenyl phosphine derivative and a specific optically active binaphthyl derivative.Type: GrantFiled: July 9, 1987Date of Patent: August 9, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshihiko Ito, Tamio Hayashi, Norio Kawamura, Ichiki Takemoto
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Patent number: 4752417Abstract: Alpha-isopropyl-p-chlorophenylacetic acid, which is an acid moiety of the pyrethroidal ester pesticides is subjected to optical resolution using optically active alpha-phenyl-beta-p-tolylethylamine or optically active alpha-phenylethylamine, as the optical resolution agent. The reaction of the acid with the amine is carried out in a hydrophobic organic solvent, such as aliphatic and aromatic hydrocarbons, in the presence of water, until the desired salt of the acid with the amine is separated therein through selective crystallization.Type: GrantFiled: June 19, 1986Date of Patent: June 21, 1988Assignee: Sumitomo Chemical Company, LimitedInventors: Ayumu Inoue, Takeaki Umemura
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Patent number: 4749804Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: June 10, 1986Date of Patent: June 7, 1988Assignee: Syntex (U.S.A.) Inc.Inventor: George C. Schloemer
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Patent number: 4689423Abstract: An improved process for the preparation of methyl 2,3,4,5-tetrafluorobenzoylacetate is described. The process is for intermediates that lead to trifluoroquinolinic acids which in turn are used to produce antibacterial agents of the difluoro quinolinecarboxylic acid type. The process runs at room temperature, uses a safe and inexpensive base, and can be conveniently scaled up for manufacturing purposes.Type: GrantFiled: April 1, 1986Date of Patent: August 25, 1987Assignee: Warner-Lambert CompanyInventors: Vladimir G. Beylin, Om P. Goel
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Patent number: 4670586Abstract: A method for the production of an .alpha.-aryl-alkanoic acid represented by the general formula II: ##STR1## wherein R.sup.3 stands for a hydrogen atom or an alkyl group and Ar for an aromatic residue, characterized by subjecting an .alpha.-haloalkyl-aryl ketal represented by the general formula I: ##STR2## wherein Ar has the same meaning as defined above, R.sup.1 and R.sup.2 independently stand for an alkyl group and embrace the case wherein they jointly form a cyclic acetal, R.sup.3 has the same meaning as defined above, and X stands for a halogen atom to a rearrangement reaction in the presence of at least one zinc compound selected from the group consisting of oxide, hydroxide, sulfide, carbonate, and basic carbonate of zinc and subsequently hydrolyzing the product of said rearrangement reaction.Type: GrantFiled: September 10, 1985Date of Patent: June 2, 1987Assignee: Nippon Chemicals Co., Ltd.Inventors: Yuta Yabe, Takamichi Watanabe, Hisayuki Suzuki
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Patent number: 4667056Abstract: A process for preparing hydratropic acids and the esters thereof, of formula Ar--CH(CH.sub.3)--COOR where R=H or lower alkyl and Ar=phenyl possibly substituted. This process consists in reacting on the propiophenones of formula ArCOCH.sub.2 CH.sub.3, a chlorinating or brominating agent, an alcohol R'OH where R'=lower alkyl, an orthoester R.sub.1 --C(OR').sub.3 wherein R.sub.1 =H or lower alkyl, and metal zinc; then possibly hydrolyzing the esters obtained.With this process can be prepared hydratropic acids known for their anti-inflammatory activity.Type: GrantFiled: May 3, 1985Date of Patent: May 19, 1987Assignee: Delalande S.A.Inventor: Guy P. Adrian
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Patent number: 4654438Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 5, 1985Date of Patent: March 31, 1987Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4638079Abstract: Disclosed is a process for inhibiting polymerization of polymerizable ethylenically unsaturated monomers such as hydrocarbons, acids and esters, wherein a cobalt (III), nickel (II) or manganese (II) complex of N-nitrosophenylhydroxylamine is employed. A composition including a polymerizable ethylenically unsaturated monomer and the complex is also disclosed. In a preferred embodiment, polymerization of an acrylic acid or an acrylate ester is inhibited.Type: GrantFiled: January 17, 1985Date of Patent: January 20, 1987Assignee: Mallinckrodt, Inc.Inventors: Ervin B. Inskip, Joseph M. Patane
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Patent number: 4620031Abstract: Alpha-alkyl-alkanoic acids are prepared by heating at boiling temperature a mixture of an alpha-halogen-alkyl-arylketone in a saturated aliphatic diol or in a mixture of saturated aliphatic diols in the presence of a Broensted's acid and by successively alkalifying the reaction mixture.Type: GrantFiled: February 1, 1985Date of Patent: October 28, 1986Assignee: Zambon S.p.A.Inventors: Fulvio Uggeri, Graziano Castaldi, Claudio Giordano
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Patent number: 4618705Abstract: Carboxylic acid anhydrides are reacted with hydrogen to produce alkylidene diesters with high yield and with ratios of alkylidene diesters and co-product carboxylic acid near the theoretical by carrying out the reaction in the presence of a cobalt carbonyl.Type: GrantFiled: January 22, 1982Date of Patent: October 21, 1986Assignee: The Halcon SD Group, Inc.Inventor: Nabil Rizkalla
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Patent number: 4618697Abstract: This invention relates to a process for preparing an alpha-arylalkanoic acid or salt thereof which comprises the rearrangement of an alpha-halo-alkylarylketal in neutral or slightly alkaline conditions, in the presence of a dipolar aprotic diluent and of a protic substance having a high dielectric constant, and the subsequent hydrolysis of the thus obtained ester.Type: GrantFiled: February 3, 1984Date of Patent: October 21, 1986Assignee: Zambon SpAInventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4616026Abstract: Compounds of the formula ##STR1## a pharmaceutically or agriculturally acceptable acid addition salt thereof wherein R is 5-chloro-2-pyridyl, phenyl or phenyl substituted by from 1 to 3 substituents, each independently selected from F, Cl, Br, I, CF.sub.3, (C.sub.1 -C.sub.4)alkyl and (C.sub.1 -C.sub.4)alkoxy; and R.sup.1 is H, Cl, phenyl, phenyl substituted by from 1 to 3 substituents each independently selected from F, Cl, Br, I and CF.sub.3 or a heterocyclic group linked to the adjacent CF.sub.2 group by a ring carbon atom; method for their use in combatting fungal infections in plants, seeds and animals, including humans, and pharmaceutical and agricultural compositions containing them.Type: GrantFiled: July 25, 1983Date of Patent: October 7, 1986Assignee: Pfizer Inc.Inventors: Kenneth Richardson, Peter J. Whittle
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Patent number: 4614816Abstract: A carboxylic acid or an ester thereof having at least two carbon atoms more than formic acid is prepared by reacting at elevated temperature e.g. 100.degree. to 250.degree. C. formic acid or a formate ester with an olefin e.g. ethylene in the presence of, as catalyst, a Group VIII noble metal e.g. iridium, preferably promoted by iodide, to cause addition of the formic acid or ester to the olefin and form the a higher acid e.g. propionic acid or ester thereof.A strong acid such as a sulphonic acid may be used as a copromoter. The catalyst is employed in solution.Type: GrantFiled: October 13, 1983Date of Patent: September 30, 1986Assignee: BP Chemicals LimitedInventors: David J. Drury, Peter S. Williams
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Patent number: 4608441Abstract: Process for preparing an arylalkanoic acid by adding iodine to a mixture of an arylalkanone and an excess of an orthoester, heating of the mixture thus obtained, adding an inorganic base and finally an acid.Type: GrantFiled: July 12, 1985Date of Patent: August 26, 1986Assignee: BLASCHIM S.p.A.Inventors: Attilio Citterio, Laura Tinucci, Aldo Belli, Lucio Filippini
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Patent number: 4605758Abstract: Pharmaceutically useful optically active .alpha.-arylalkanoic acids or esters, ortho esters, or amides thereof are stereoselectively prepared by contacting an aryl magnesium Grignard reagent with an optically active .alpha.-substituted acyl halide to form the optically active aryl .alpha.-substituted alkyl ketone, which is ketalized and rearranged to the desired optically active .alpha.-arylalkanoic acid or the corresponding ester, ortho ester or amide. In an alternate embodiment, the aryl .alpha.-substituted alkyl ketone is reduced to the corresponding alkanol, which is rearranged to the .alpha.-arylalkanal. The alkanal so produced is converted to the desired optically active .alpha.-arylalkanoic acid by conventional methods.Type: GrantFiled: April 23, 1984Date of Patent: August 12, 1986Assignee: Syntex Pharmaceuticals International Ltd.Inventor: George C. Schloemer
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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: 4594450Abstract: A process for producing an .alpha.-halogeno-.beta.-phenylpropionic acid represented by the general formula: ##STR1## where X is a halogen atom, which comprises hydrolyzing under heating a halogen-containing ethylbenzene derivative represented by the general formula: ##STR2## where W is a cyano group, an amidocarbonyl group or a lower alkoxycarbonyl group, and X is as defined above, in an aqueous mineral acid solution under vigorous stirring.Type: GrantFiled: October 12, 1984Date of Patent: June 10, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kiyotaka Oyama, Tuneo Harada
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Patent number: 4577025Abstract: A method for the preparation of an ester of .alpha.-thio-.alpha.-aromatic propionic acid derivatives of the formula: ##STR1## wherein R.sup.1 is alkyl, phenyl or benzothiazolyl, R.sup.2 is alkyl and Ar is an aromatic substituent.The method comprises reacting an ester of .alpha.-chloro-.alpha.-thiopropionic acid of the formula: ##STR2## with an aromatic compound of the formula ARH, in the presence of a Lewis acid. The method provides good reactivity and positional selectivity in the Friedel-Crafts reaction. Many esters of the formula (2) are useful as pharmaceuticals, agricultural chemicals, perfumes or their intermediates.Type: GrantFiled: August 26, 1983Date of Patent: March 18, 1986Assignee: Nissan Chemical Industries, Ltd.Inventors: Kazutaka Arai, Yoshio Ohara, Yashio Takakuwa, Toyoko Iizumi
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Patent number: 4570017Abstract: A process for the preparation of an optically-active (mixed) anhydride of an alpha-chiral (optically-active) carboxylic acid by treating a non-symmetrical ketene with a carboxylic acid in the presence of an optically-active (chiral) tertiary amine catalyst. Hydrolysis of the resulting (mixed) anhydride yields the optically-active acid corresponding to the non-symmetrical ketene.Type: GrantFiled: March 26, 1984Date of Patent: February 11, 1986Assignee: Shell Oil CompanyInventor: Donald W. Stoutamire
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Patent number: 4567293Abstract: A novel compound of 2-[para-(2-substituted or unsubstituted-3,3,3-trifluoropropyl)phenyl]propionic acid or a salt thereof which has a specific pharmacological activity and a pharmaceutical composition comprising the novel compound as an active ingredient are disclosed.Type: GrantFiled: February 20, 1985Date of Patent: January 28, 1986Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Takashi Yamauchi, Akira Iizuka
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Patent number: 4562284Abstract: A process is disclosed for preparation of a carboxylic acid RCOOH wherein R represents certain alkyl, cycloalkyl or aralkyl groups, by heating a formic acid ester HCOOR in the presence of carbon monoxide, a soluble rhodium catalyst and an iodide or bromide source, promoted by certain oxygen-containing compounds of phosphorus, arsenic or antimony.Type: GrantFiled: February 24, 1984Date of Patent: December 31, 1985Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4558153Abstract: Carboxylic acids having two or more carbon atoms than formic acid, or esters of such carboxylic acids are prepared by reacting either formic acid or an ester of formic acid with an olefin at elevated temperature in the presence of a Group VIB metal catalyst. The Group VIB metal which is chromium, molybdenum or tungsten is suitably added as a carbonyl or carbonyl halide. In addition to the catalyst a halide promoter and a phosphorus containing copromoter may optionally be added. The process can be used, for example to prepare propionic acid or a propionic acid ester from ethylene and either formic acid of an ester of formic acid.Type: GrantFiled: October 23, 1984Date of Patent: December 10, 1985Assignee: BP Chemicals LimitedInventor: John Cook
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Patent number: 4544766Abstract: This invention relates to a process for preparing an aryl acetic acid derivative represented by the formulaAr--CH.sub.2 COY).sub.ncomprising hydrolyzing in an alkaline substance a dichloroethenyl compound represented by the formulaAr--CH.dbd.CCl.sub.2).sub.n.Type: GrantFiled: February 26, 1982Date of Patent: October 1, 1985Assignee: Otsuka Kagaku Yakuhin Kabushiki KaishaInventor: Tatsuya Shono
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Patent number: 4542237Abstract: .alpha.-Arylalkanoic acids or esters, orthoesters or amides thereof are prepared by forming an .alpha.-hydroxy ketal or thioketal of an aryl alkyl ketone, activating the .alpha.-hydroxy substituent with an esterifying agent to form the corresponding ketal or thioketal ester substrate, wherein the ester group is sufficiently labile to non-catalytically disassociate from the substrate in a protic or dipolar, aprotic solvent, maintaining the ester substrate in contact with the protic or dipolar, aprotic solvent or mixtures thereof for a time sufficient to form the corresponding .alpha.-arylakanoic acid or ester, orthoester or amide thereof, and optionally concomitantly or sequentially hydrolyzing any ester, orthoester or amide formed to the corresponding .alpha.-arylalkanoic acid.Type: GrantFiled: June 7, 1983Date of Patent: September 17, 1985Assignee: Syntex Pharmaceuticals International LimitedInventor: George C. Schloemer
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Patent number: 4536342Abstract: A process for producing a halogen-containing ethylbenzene derivative represented by the general formula: ##STR1## where X is a halogen atom, and Y is a nitrile group, a carboxyl group, a lower alkoxycarbonyl group or an amidocarbonyl group, which comprises reacting a vinyl compound represented by the general formula:CH.sub.2 .dbd.CH--Y (II)where Y is as defined above, with a benzenediazonium salt and halogen ions in a solvent mixture comprising a lower alcohol and/or an ether, and water, under an acidic condition with a mineral acid, in the presence of a monovalent copper compound as a catalyst.Type: GrantFiled: October 5, 1984Date of Patent: August 20, 1985Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kiyotaka Oyama, Tuneo Harada
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Patent number: 4534909Abstract: A process for producing a halogen-containing ethylbenzene derivative represented by the general formula: ##STR1## where X is a halogen atom, and W is a nitrile group, a carboxyl group, a lower alkoxycarbonyl group or an amidocarbonyl group, which comprises diazotizing aniline with a nitrite in a solution mixture comprising a hydrophilic organic solvent, an aqueous mineral acid solution and a vinyl compound represented by the general formula:CH.sub.2 .dbd.CH--W (II)where W is as defined above, to form a benzenediazonium salt, and reacting the benzenediazonium salt, without isolating it from the reaction system, with said vinyl compound in the presence of halogen ions and a copper compound as a catalyst.Type: GrantFiled: October 12, 1984Date of Patent: August 13, 1985Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kiyotaka Oyama, Tuneo Harada
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Patent number: 4535166Abstract: Rearrangement of alpha-halo-alkylarylketals in neutral or weakly alkaline conditions and in the presence of a polar-protic medium and subsequent hydrolysis of the thus obtained esters, in the same reaction medium, to afford the corresponding alpha-arylalkanoic acids or their salts which are particularly useful as anti-inflammatory, analgesic and antipyretic agents.Type: GrantFiled: August 3, 1983Date of Patent: August 13, 1985Assignee: Zambon S.p.A.Inventors: Graziano Castaldi, Claudio Giordano
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Patent number: 4529810Abstract: Optically-active alpha-substituted carboxylic esters are prepared by treating a non-symmetrical ketene with an alcohol in the presence of an optically-active amine catalyst. Hydrolysis of the resulting esters, yields the optically-active acid corresponding to the non-symmetrical ketene.Type: GrantFiled: January 6, 1984Date of Patent: July 16, 1985Assignee: Shell Oil CompanyInventor: Donald W. Stoutamire
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Patent number: 4523033Abstract: The compound 15-(p-[.sup.125 I]-iodophenyl)-6-tellurapentadecanoic acid is disclosed as a myocardial imaging agent having rapid and pronounced uptake, prolonged myocardial retention, and low in vivo deiodination.Type: GrantFiled: June 29, 1983Date of Patent: June 11, 1985Assignee: The United States of America as represented by the United States Department of EnergyInventors: Furn F. Knapp, Jr., Mark M. Goodman
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Patent number: 4515970Abstract: A process for preparation of substituted acetic acids having the general formula I:Ar--CHR--COOH Iin which R is selected from the group consisting in one hydrogen atom and C.sub.1 -C.sub.4 -alkyl radicals, and Ar is selected from the group consisting in radicals of aromatic nature selected from the following radicals: 2-thienyl, 2-methoxy-1-naphthyl, 3,4-methylenedioxy-phenyl, and the substituted phenyls of the general formula II: ##STR1## where R.sub.1 is selected from the group consisting in hydrogen and C.sub.1 -C.sub.4 -alkyl groups, and R.sub.Type: GrantFiled: April 17, 1984Date of Patent: May 7, 1985Assignee: Societe Francaise HoechstInventors: Yani Christidis, Jean-Claude Vallejos
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Patent number: 4501913Abstract: Process for preparing esters of aryl alkanoic acids via oxidation of the corresponding ketones with bromine or iodine in the presence of a metal halide and an alcohol.The thus obtained esters are then easily hydrolized to give the corresponding aryl alkanoic acids which are particularly useful as anti-inflammatory, analgesic and anti-pyretic agents.Type: GrantFiled: November 1, 1983Date of Patent: February 26, 1985Assignee: Zambon S.p.A.Inventors: Claudio Giordano, Graziano Castaldi
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Patent number: 4496736Abstract: Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200.degree. to 350.degree. C.Type: GrantFiled: June 3, 1982Date of Patent: January 29, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
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Patent number: 4465855Abstract: Arylacetic acid derivatives of the formula ##STR1## with R.sup.1, R.sup.2 and R.sup.3 specifically defined and which are useful as antirheumatic and antiinflammatory pharmaceuticals are prepared by catalytic hydrogenation of new compounds of the formula ##STR2## in which R and R.sup.10 are also specifically defined. The method of making the latter compound is also set forth.Type: GrantFiled: April 15, 1982Date of Patent: August 14, 1984Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara RtInventors: Endre Palosi, Dezso Korbonits, Pal Kiss, Csaba Gonczy, Gergely Heja, Judit Cser nee Kun, Rudolf Szebeni, Maria Szomor nee Wundele, Ida Szvoboda nee Kanzel
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Patent number: 4464300Abstract: There are presented benzazepines of the formula ##STR1## wherein either R.sup.1 is hydrogen, lower alkyl, 4-pyridyl or the group --(CH.sub.2).sub.n --NR.sup.6 R.sup.7 and R.sup.2 and R.sup.3 together are an additional bond or R.sup.1 and R.sup.2 together are the oxo group and R.sup.3 is hydrogen or lower alkyl, R.sup.4 is phenyl, o-halophenyl or 2-pyridyl, R.sup.5 is halogen or nitro and either R.sup.6 is hydrogen or lower alkyl and R.sup.7 is hydrogen, lower alkyl, lower alkenyl or lower alkynyl or R.sup.6 and R.sup.7 together with the nitrogen atom are 4-(lower alkyl)-1-piperazinyl or 4-morpholinyl and n is the number 0 or 1, and their pharmaceutically acceptable acid additions salts.The compounds possess interesting psychotropic properties, i.e., pronounced anxiolytic properties have been established in the case of certain representative members of this class of substance.Type: GrantFiled: July 15, 1982Date of Patent: August 7, 1984Assignee: Hoffmann-La Roche Inc.Inventors: Rene Borer, Max Gerecke, Emilio Kyburz
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Patent number: 4440947Abstract: Substituted .alpha.-halogenopropionic acids and their derivatives of the general formula ##STR1## wherein R.sup.1 to R.sup.3, Y and X have the meanings given in the description, are prepared by a process which is characterized in that substituted vinylidene chlorides of the general formula ##STR2## are reacted with chlorine or bromine chloride in the presence of compounds of the formulaR.sup.5 --SO.sub.3 R.sup.6 (III)wherein R.sup.5 and R.sup.6 have the meaning given in the description, and the products obtained are treated, if appropriate, with water or alcohol. Certain of the substituted .alpha.-halogeno-propionic acids and the substituted vinylidene chloride of the formula ##STR3## are new. The end products are useful as herbicides and intermediates for insecticides.Type: GrantFiled: March 5, 1982Date of Patent: April 3, 1984Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 4440936Abstract: The chiral phosphine ligand (R)-1,2-bis(diphenylphosphino)-1-cyclohexylethane, when complexed to Rh(I), functions as a superior chiral hydrogenation catalyst. The chiral phosphine ligand is more stereochemically rigid than previous compounds; consequently, virtually optically pure materials can be produced from the chiral hydrogenation of prochiral compounds using the catalyst of this invention. This catalyst is especially useful in the chiral hydrogenation of alpha-acylamido acrylic acids.Type: GrantFiled: January 18, 1982Date of Patent: April 3, 1984Assignee: The Procter & Gamble CompanyInventor: Dennis P. Riley
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Patent number: 4433160Abstract: A process for producing an .alpha.-arylalkanoic acid ester represented by the general formula ##STR1## wherein Ar represents an aryl group which may optionally be substituted, and R.sup.1 and R.sup.2, independently from each other, represent a lower alkyl group,which comprises reacting a Grignard reagent prepared from an aryl halide of the general formulaAr--X.sup.1 (II)wherein Ar is as defined above and X.sup.1 represents a halogen atom,and magnesium, with an .alpha.-haloalkanoic acid ester of the general formula ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and X.sup.2 represents a halogen atom,said reaction of the Grignard reagent with the .alpha.-haloalkanoic acid ester of general formula (III) being carried out in the presence of a nickel compound.Type: GrantFiled: August 25, 1982Date of Patent: February 21, 1984Assignee: Taisho Pharmaceutical Company, Ltd.Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
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Patent number: 4431835Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) chromium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 14, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron
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Patent number: 4430506Abstract: Alkyl carboxylates are hydrocarbonylated and/or carbonylated with carbon monoxide and hydrogen, in an aqueous medium, and in the presence of a catalytically effective amount of a catalyst system comprising (i) ruthenium, (ii) cobalt, (iii) at least one iodine-containing promoter, and (iv) vanadium. The subject hydrocarbonylation/carbonylation is admirably well suited, e.g., for the preparation of acetaldehyde, ethanol, ethyl acetate and acetic acid, especially from a methyl carboxylate.Type: GrantFiled: July 6, 1981Date of Patent: February 7, 1984Assignee: Rhone-Poulenc IndustriesInventors: Jean Gauthier-Lafaye, Robert Perron