Carboxyl, Or Salt Thereof, Not Bonded Directly To Ring Patents (Class 562/496)
  • Patent number: 4927967
    Abstract: 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: Grant
    Filed: November 6, 1985
    Date of Patent: May 22, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Richard W. Wegman
  • Patent number: 4922009
    Abstract: 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: Grant
    Filed: December 23, 1987
    Date of Patent: May 1, 1990
    Assignee: Zambon SpA
    Inventors: Marco Villa, Claudio Giordano, Graziano Castaldi, Silvia Cavicchioli
  • Patent number: 4918226
    Abstract: 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: Grant
    Filed: June 22, 1981
    Date of Patent: April 17, 1990
    Assignee: Exxon Research and Engineering Company
    Inventor: Roy L. Pruett
  • Patent number: 4910337
    Abstract: .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: Grant
    Filed: January 27, 1989
    Date of Patent: March 20, 1990
    Assignee: Mine Safety Appliances Company
    Inventors: Kuen-Wai Chiu, Mary H. Staruch, David H. Ellenberger
  • Patent number: 4897473
    Abstract: 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: Grant
    Filed: May 1, 1981
    Date of Patent: January 30, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: Bernard D. Dombek
  • Patent number: 4883916
    Abstract: 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: Grant
    Filed: April 1, 1988
    Date of Patent: November 28, 1989
    Assignee: Eisai Co., Ltd.
    Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
  • Patent number: 4864038
    Abstract: 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: Grant
    Filed: June 10, 1988
    Date of Patent: September 5, 1989
    Assignee: Merck & Co., Inc.
    Inventors: William F. Hoffman, Ta J. Lee, Clarence S. Rooney
  • Patent number: 4822913
    Abstract: 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: Grant
    Filed: October 28, 1983
    Date of Patent: April 18, 1989
    Assignee: Amoco Corporation
    Inventor: Gary P. Hagen
  • Patent number: 4801719
    Abstract: 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: Grant
    Filed: June 8, 1987
    Date of Patent: January 31, 1989
    Assignee: Ciba-Geigy Corporation
    Inventors: Konrad Oertle, Hansjurg Wetter
  • Patent number: 4788330
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: November 29, 1988
    Assignee: Eisai Co., Ltd.
    Inventors: Kouji Nakamoto, Takeshi Suzuki, Shinya Abe, Kenji Hayashi, Akiharu Kajiwara, Isao Yamatsu, Issei Otsuka, Hiroyuki Shiojiri
  • Patent number: 4786744
    Abstract: 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: Grant
    Filed: June 17, 1985
    Date of Patent: November 22, 1988
    Assignee: Centre National de la Recherche Scientifique
    Inventors: Albert L. F. Robert, Jean-Luc Guinamant, Sylvie C. A. Jaguelin
  • Patent number: 4762948
    Abstract: 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: Grant
    Filed: July 9, 1987
    Date of Patent: August 9, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshihiko Ito, Tamio Hayashi, Norio Kawamura, Ichiki Takemoto
  • Patent number: 4752417
    Abstract: 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: Grant
    Filed: June 19, 1986
    Date of Patent: June 21, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ayumu Inoue, Takeaki Umemura
  • Patent number: 4749804
    Abstract: 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: Grant
    Filed: June 10, 1986
    Date of Patent: June 7, 1988
    Assignee: Syntex (U.S.A.) Inc.
    Inventor: George C. Schloemer
  • Patent number: 4689423
    Abstract: 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: Grant
    Filed: April 1, 1986
    Date of Patent: August 25, 1987
    Assignee: Warner-Lambert Company
    Inventors: Vladimir G. Beylin, Om P. Goel
  • Patent number: 4670586
    Abstract: 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: Grant
    Filed: September 10, 1985
    Date of Patent: June 2, 1987
    Assignee: Nippon Chemicals Co., Ltd.
    Inventors: Yuta Yabe, Takamichi Watanabe, Hisayuki Suzuki
  • Patent number: 4667056
    Abstract: 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: Grant
    Filed: May 3, 1985
    Date of Patent: May 19, 1987
    Assignee: Delalande S.A.
    Inventor: Guy P. Adrian
  • Patent number: 4654438
    Abstract: .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: Grant
    Filed: June 5, 1985
    Date of Patent: March 31, 1987
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer
  • Patent number: 4638079
    Abstract: 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: Grant
    Filed: January 17, 1985
    Date of Patent: January 20, 1987
    Assignee: Mallinckrodt, Inc.
    Inventors: Ervin B. Inskip, Joseph M. Patane
  • Patent number: 4620031
    Abstract: 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: Grant
    Filed: February 1, 1985
    Date of Patent: October 28, 1986
    Assignee: Zambon S.p.A.
    Inventors: Fulvio Uggeri, Graziano Castaldi, Claudio Giordano
  • Patent number: 4618705
    Abstract: 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: Grant
    Filed: January 22, 1982
    Date of Patent: October 21, 1986
    Assignee: The Halcon SD Group, Inc.
    Inventor: Nabil Rizkalla
  • Patent number: 4618697
    Abstract: 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: Grant
    Filed: February 3, 1984
    Date of Patent: October 21, 1986
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4616026
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: October 7, 1986
    Assignee: Pfizer Inc.
    Inventors: Kenneth Richardson, Peter J. Whittle
  • Patent number: 4614816
    Abstract: 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: Grant
    Filed: October 13, 1983
    Date of Patent: September 30, 1986
    Assignee: BP Chemicals Limited
    Inventors: David J. Drury, Peter S. Williams
  • Patent number: 4608441
    Abstract: 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: Grant
    Filed: July 12, 1985
    Date of Patent: August 26, 1986
    Assignee: BLASCHIM S.p.A.
    Inventors: Attilio Citterio, Laura Tinucci, Aldo Belli, Lucio Filippini
  • Patent number: 4605758
    Abstract: 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: Grant
    Filed: April 23, 1984
    Date of Patent: August 12, 1986
    Assignee: Syntex Pharmaceuticals International Ltd.
    Inventor: George C. Schloemer
  • Patent number: 4604243
    Abstract: 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: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4594450
    Abstract: 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: Grant
    Filed: October 12, 1984
    Date of Patent: June 10, 1986
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kiyotaka Oyama, Tuneo Harada
  • Patent number: 4577025
    Abstract: 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: Grant
    Filed: August 26, 1983
    Date of Patent: March 18, 1986
    Assignee: Nissan Chemical Industries, Ltd.
    Inventors: Kazutaka Arai, Yoshio Ohara, Yashio Takakuwa, Toyoko Iizumi
  • Patent number: 4570017
    Abstract: 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: Grant
    Filed: March 26, 1984
    Date of Patent: February 11, 1986
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4567293
    Abstract: 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: Grant
    Filed: February 20, 1985
    Date of Patent: January 28, 1986
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Kobayashi, Itsumaro Kumadaki, Takashi Yamauchi, Akira Iizuka
  • Patent number: 4562284
    Abstract: 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: Grant
    Filed: February 24, 1984
    Date of Patent: December 31, 1985
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4558153
    Abstract: 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: Grant
    Filed: October 23, 1984
    Date of Patent: December 10, 1985
    Assignee: BP Chemicals Limited
    Inventor: John Cook
  • Patent number: 4544766
    Abstract: 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: Grant
    Filed: February 26, 1982
    Date of Patent: October 1, 1985
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventor: Tatsuya Shono
  • Patent number: 4542237
    Abstract: .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: Grant
    Filed: June 7, 1983
    Date of Patent: September 17, 1985
    Assignee: Syntex Pharmaceuticals International Limited
    Inventor: George C. Schloemer
  • Patent number: 4536342
    Abstract: 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: Grant
    Filed: October 5, 1984
    Date of Patent: August 20, 1985
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kiyotaka Oyama, Tuneo Harada
  • Patent number: 4534909
    Abstract: 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: Grant
    Filed: October 12, 1984
    Date of Patent: August 13, 1985
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kiyotaka Oyama, Tuneo Harada
  • Patent number: 4535166
    Abstract: 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: Grant
    Filed: August 3, 1983
    Date of Patent: August 13, 1985
    Assignee: Zambon S.p.A.
    Inventors: Graziano Castaldi, Claudio Giordano
  • Patent number: 4529810
    Abstract: 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: Grant
    Filed: January 6, 1984
    Date of Patent: July 16, 1985
    Assignee: Shell Oil Company
    Inventor: Donald W. Stoutamire
  • Patent number: 4523033
    Abstract: 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: Grant
    Filed: June 29, 1983
    Date of Patent: June 11, 1985
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Furn F. Knapp, Jr., Mark M. Goodman
  • Patent number: 4515970
    Abstract: 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: Grant
    Filed: April 17, 1984
    Date of Patent: May 7, 1985
    Assignee: Societe Francaise Hoechst
    Inventors: Yani Christidis, Jean-Claude Vallejos
  • Patent number: 4501913
    Abstract: 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: Grant
    Filed: November 1, 1983
    Date of Patent: February 26, 1985
    Assignee: Zambon S.p.A.
    Inventors: Claudio Giordano, Graziano Castaldi
  • Patent number: 4496736
    Abstract: 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: Grant
    Filed: June 3, 1982
    Date of Patent: January 29, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Bonse, Gerhard Marzolph, Heinz U. Blank
  • Patent number: 4465855
    Abstract: 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: Grant
    Filed: April 15, 1982
    Date of Patent: August 14, 1984
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt
    Inventors: Endre Palosi, Dezso Korbonits, Pal Kiss, Csaba Gonczy, Gergely Heja, Judit Cser nee Kun, Rudolf Szebeni, Maria Szomor nee Wundele, Ida Szvoboda nee Kanzel
  • Patent number: 4464300
    Abstract: 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: Grant
    Filed: July 15, 1982
    Date of Patent: August 7, 1984
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Rene Borer, Max Gerecke, Emilio Kyburz
  • Patent number: 4440947
    Abstract: 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: Grant
    Filed: March 5, 1982
    Date of Patent: April 3, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 4440936
    Abstract: 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: Grant
    Filed: January 18, 1982
    Date of Patent: April 3, 1984
    Assignee: The Procter & Gamble Company
    Inventor: Dennis P. Riley
  • Patent number: 4433160
    Abstract: 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: Grant
    Filed: August 25, 1982
    Date of Patent: February 21, 1984
    Assignee: Taisho Pharmaceutical Company, Ltd.
    Inventors: Takehiro Amano, Kensei Yoshikawa, Tatsuhiko Sano, Yutaka Ohuchi, Michihiro Ishiguro, Manzo Shiono, Yoshiji Fujita, Takashi Nishida
  • Patent number: 4431835
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: February 14, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean Gauthier-Lafaye, Robert Perron
  • Patent number: 4430506
    Abstract: 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: Grant
    Filed: July 6, 1981
    Date of Patent: February 7, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Jean Gauthier-Lafaye, Robert Perron