Carboxyl, Or Salt Thereof, Not Bonded Directly To Ring Patents (Class 562/496)
-
Patent number: 4417073Abstract: A process for the preparation of substituted acetic acids and derivatives thereof, having the formula ##STR1## wherein X is --COOH, --COOY or --CN,Y is --CH.sub.3 or --C.sub.2 H.sub.5,R.sub.1 is a saturated, branched or unbranched aliphatic radical having from 1 to 6 carbon atoms, a phenyl radical, or a phenyl radical substituted by alkyl or alkoxy groups, andR.sub.2 is hydrogen or a saturated, branched or unbranched aliphatic radical having from 1 to 6 carbon atoms, a phenyl radical, or a phenyl radical substituted by alkyl or alkoxy groups,wherein R.sub.1 and R.sub.2 may be the same or different which process comprises converting the corresponding malonic or cyanoacetic ester of the formula ##STR2## wherein Z is --COOY or --CN, andY, R.sub.1 and R.sub.2 are identified as above at elevated temperature in the presence of a catalyst, e.g., a catalyst containing from about 50 to 75 weight percent SiO.sub.2 and from 15 to 19 weight percent Al.sub.2 O.sub.Type: GrantFiled: November 25, 1981Date of Patent: November 22, 1983Assignee: Dynamit Nobel A.G.Inventors: Otto Ackermann, Gerhard Daum
-
Patent number: 4410734Abstract: S-Configurated phenylpropane derivatives of the formula ##STR1## where R.sup.1 is alkyl, aryl or alkoxy, R.sup.2 is hydrogen, alkyl, aryl or alkoxy, and R.sup.3 is carboxyl or esterified carboxyl, acetalized formyl, hydroxymethyl or esterified hydroxymethyl, their preparation by microbiological hydrogenation, and their use for the preparation of fungicidal compounds.Type: GrantFiled: December 8, 1980Date of Patent: October 18, 1983Assignee: BASF AktiengesellschaftInventors: Christoph Martin, Walter Himmele, Hardo Siegel
-
Patent number: 4409397Abstract: Tetra-substituted olefinic acids and derivatives of the formula ##STR1## wherein R is --COOM in which M is a cation forming a soluble salt or --COOR.sup.4 or --CON(R.sup.4).sub.2 in which each R.sup.4 is independently a hydrogen atom or an alkyl group; R.sup.1 is an optionally substituted alkyl, cycloalkyl, aryl or heterocyclic group; and R.sup.2 or R.sup.3 each independently is an optionally substituted alkyl or cycloalkyl group or R.sup.2 and R.sup.3 together with the carbon atom to which they are attached form a carbocyclic ring, are asymmetrically hydrogenated in the presence of a coordinated complex of rhodium, iridium, or ruthenium in combination with a chiral metallocenylphosphine or pyrrolidinylphosphine ligand.Type: GrantFiled: May 6, 1982Date of Patent: October 11, 1983Assignee: Shell Oil CompanyInventor: Timm E. Paxson
-
Patent number: 4407757Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.Type: GrantFiled: December 31, 1980Date of Patent: October 4, 1983Assignee: Takeda Chemical Industries, Ltd.Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada
-
Patent number: 4388322Abstract: Substituted 3-(1,2-dibromo-alkyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters of the formula ##STR1## in which R.sup.1 is halogen or optionally substituted phenyl or optionally substituted alkyl,R.sup.2 is hydrogen, halogen or optionally substituted alkyl, andY is the radical of an alcohol customary in pyrethroids, with the proviso that Y is a benzyloxy radical which is substituted by halogen and optionally substituted by at least one additional radical if R.sup.1 is halogen or methyl,which possess pesticidal properties. The acid moieties of such esters wherein R.sup.1 is optionally substituted phenyl are new compounds.Type: GrantFiled: January 19, 1981Date of Patent: June 14, 1983Assignee: Bayer AktiengesellschaftInventors: Rainer Fuchs, Klaus Naumann, Ingeborg Hammann, Wilhelm Stendel
-
Patent number: 4376213Abstract: A method for optical resolution of 2-(4-chlorophenyl)-3-methylbutanoic acid, which comprises crystallizing out the salt between (+) or (-)-2-(4-chlorophenyl)-3-methylbutanoic acid and diethylamine in a molar proportion of 2:1 predominantly from a super-saturated solution of the salt of 2-(4-chlorophenyl)-3-methylbutanoic acid with diethylamine, collecting the crystallized salt and decomposing the collected salt under acidic conditions to obtain the corresponding optically active acid.Type: GrantFiled: February 1, 1982Date of Patent: March 8, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Hiroyuki Nohira, Daiyo Terunuma, Shinji Koube
-
Patent number: 4355168Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.Type: GrantFiled: December 2, 1980Date of Patent: October 19, 1982Assignee: Montedison S.p.A.Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
-
Patent number: 4347373Abstract: This invention relates to a series of compounds having therapeutic activity, consisting of the derivatives obtained by reacting 4-methyl-5-[(2-aminoethyl)-thiomethyl]-imidazole with non-steroidal, traditional, antiinflammatory agents. The derivatives are carboxamides of formula ##STR1## wherein R.sub.1 =H; --CH.sub.3 ; --C.sub.2 H.sub.5 ; and ##STR2## of the antiinflammatory agents, i.e. the acylic radical of the antiinflammatory acid, or ##STR3## of the antiinflammatory acid and the corresponding physiologically acceptable salts on the imidazole ring.Type: GrantFiled: March 9, 1981Date of Patent: August 31, 1982Inventor: Franco Turconi
-
Patent number: 4335251Abstract: The present invention relates to the phenyl-propionic acid ester derivative of the following formula: ##STR1## The compound obtained by the present invention possesses a high degree of analgetic, antipyretic and anti-inflammatory activity and causes little side effects on the gastro-intestinal tracts, when administered orally and topically, and it may be useful as an oral and topical analgesic, antipyretic and anti-inflammatory agent.Type: GrantFiled: August 5, 1980Date of Patent: June 15, 1982Assignee: Hisamitsu Pharmaceutical Co. Inc.Inventors: Kanji Noda, Akira Nakagawa, Yuji Ishikura, Hiroyuki Ide
-
Patent number: 4334094Abstract: This invention pertains to the production of higher homologues of aliphatic carboxylic acids by reaction of said acids with carbon monoxide and hydrogen in the presence of one or more palladium-containing catalysts in combination with a Group VB tertiary donor ligand and in the presence of an iodide or bromide promoter.Type: GrantFiled: June 30, 1980Date of Patent: June 8, 1982Assignee: Texaco Inc.Inventor: John F. Knifton
-
Patent number: 4307034Abstract: An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inert organic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide and cooling the dispersion. The dispersion of alkali hydroxide is used in a reaction of an active methylene compound with an organoalkyl halide such as a reaction of a halophenylacetonitrile with an isopropyl halide to obtain .alpha.-isopropyl halophenylacetonitrile.Type: GrantFiled: September 13, 1979Date of Patent: December 22, 1981Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
-
Patent number: 4268442Abstract: There are disclosed processes for preparing an aromatic acetic acid by the reaction of an aromatic aldehyde with a combination of a trihalomethane and an alkanethiol, and by the reaction of an alcohol derivative (2,2,2-trihalo-1-arylethanol) with an alkanethiol, in the presence of a base in a mixed medium of water and an aprotic polar solvent.Type: GrantFiled: November 13, 1979Date of Patent: May 19, 1981Assignee: Sagami Chemical Research CenterInventors: Kiyosi Kondo, Tamotsu Fujimoto, Minoru Suda, Daiei Tunemoto
-
Patent number: 4268687Abstract: The present invention provides a novel process for the production of methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid. The process comprises the steps of:(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,(b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide,(c) hydrolyzing the benzoyl cyanide to produce the corresponding keto-acid,(d) hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid,(e) hydrogenating (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid in the presence of glacial acetic acid to produce the corresponding substituted acetic acid, and(f) esterifying the substituted acetic acid using an alcohol selected from the group consisting of methyl and ethyl to obtain the corresponding methyl or ethyl ester of (3-trifluoromethylphenyl)-acetic acid.Type: GrantFiled: November 7, 1979Date of Patent: May 19, 1981Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
-
Patent number: 4263443Abstract: Hydrocarbons and esters and/or acids are produced by heating aldehydes in the presence of an alcohol or an alcohol equivalent and in the presence of an iodine or bromine moiety and a rhodium or iridium catalyst.Type: GrantFiled: November 22, 1978Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: John F. White
-
Patent number: 4245116Abstract: A method for racemization of optically active 2-(4-chlorophenyl)-3-methylbutyric acid which comprises the steps of (a) reacting optically active 2-(4-chlorophenyl)-3-methylbutyric acid with a hydroxide or carbonate of an alkali metal or alkaline earth metal at a temperature of more than 110.degree. C. to produce a racemate of the alkali metal or alkaline earth metal salt of the above acid, and (b) converting the resulting racemate of the salt to the acid.Type: GrantFiled: December 11, 1978Date of Patent: January 13, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Nobuo Ohno, Masakazu Miyakado, Hajime Hirai
-
Patent number: 4238413Abstract: The present invention relates to a novel organic compound, (3-trifluoromethyl)-benzoyl cyanide, and a process for the preparation thereof comprising(a) converting (3-trifluoromethyl)-benzotrichloride to the corresponding benzoyl chloride,b) cyanation of the benzoyl chloride to produce the corresponding benzoyl cyanide, (3-trifluoromethyl)-benzoyl cyanide.Type: GrantFiled: November 7, 1979Date of Patent: December 9, 1980Assignee: Hooker Chemicals & Plastics Corp.Inventors: David Y. Tang, Arthur M. Foster
-
Patent number: 4238358Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.Type: GrantFiled: March 29, 1979Date of Patent: December 9, 1980Assignee: Western Kentucky UniversityInventors: Norman L. Holy, William A. Logan, Karl D. Stein
-
Patent number: 4237314Abstract: Phenyl acetic acid is prepared by the reaction of molecular oxygen and the combination of acetic acid and benzene in the presence of a catalytic system featuring both tellurium and halide, the unit atomic ratio of halide to tellurium being within a range from about 3 to about 20, at a temperature within a range from about 100.degree. C. to about 200.degree. C. at a pressure within a range from about 1 to about 15 atmospheres.Type: GrantFiled: September 6, 1979Date of Patent: December 2, 1980Assignee: Atlantic Richfield CompanyInventors: Ming N. Sheng, Jar-Lin Kao
-
Patent number: 4227016Abstract: Glyoxylic acid and hydrochloric acid are reacted with an aromatic compound having at least one substituent group selected from among the alkyl, aryl, hydroxy, alkoxy and aryloxy groups. The glyoxylic acid is used in a concentration comprised between 60 and 100% and the hydrochloric acid is used in as concentrated an aqueous solution as possible, e.g. in an organic solvent medium such as acetic acid. An acid catalyst such as zinc chloride may be used. The reaction may be carried out under pressure. The products are useful in various syntheses e.g. to produce amino acids or arylacetic acids with medicinal uses.Type: GrantFiled: December 28, 1977Date of Patent: October 7, 1980Assignee: Hoechst FranceInventors: Emmanuel Herman, Helmut Diery, Michel Soreau, Yani Christidis
-
Patent number: 4220592Abstract: A substituted acetonitrile such as .alpha.-isopropyl-p-chlorophenylacetonitrile is hydrolyzed using an acid to produce the corresponding substituted phenylacetic acid such as .alpha.-isopropyl-p-chlorophenylacetic acid in such a manner that, in a lot in any one hydrolysis reaction, (1) the hydrolysis is carried out in at least two steps, (2) an acid to be used in a subsequent first reaction step is a waste acid produced in a previous second reaction step and the subsequent reaction step(s) thereof if any, and (3) an acid to be used in a second reaction step and the subsequent reaction step(s) if any, is the waste acid produced in a previous second reaction step and subsequent reaction step(s), respectively, and a fresh acid.Type: GrantFiled: July 10, 1978Date of Patent: September 2, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Keiji Kagawa, Naoya Kanda, Fujio Masuko, Hirotoshi Nakanishi
-
Patent number: 4215044Abstract: Process for preparing an organic compound of the formula R.sup.2 R.sup.2 CFC(O)R.sup.3, which process comprises contacting and reacting in a reaction mixture which includes an inert solvent, at a temperature of -40.degree. C. to -100.degree. C., ROF and ##STR1## R is polyfluoroperhaloalkyl of 1-6 carbon atoms or FOCF.sub.2 ; R.sup.1 is hydrocarbyl of 1-6 carbon atoms;each R.sup.2 is selected from H, alkyl of 1-17 carbon atoms, cycloalkyl of 3-6 carbon atoms, aryl, heteroaryl and such alkyl, cycloalkyl, aryl and heteroaryl substituted by halogen or alkoxy of 1-6 carbon atoms;R.sup.3 is selected from H, alkyl and haloalkyl of 1-16 carbon atoms, cycloalkyl of 3-10 carbon atoms, aryl and haloaryl, OSi(R.sup.1).sub.3, OH, NH.sub.2, alkoxy of 1-6 carbon atoms, aryloxy, NHR.sup.1 and NR.sup.1.sub.2 wherein R.sup.1 is alkyl of 1-6 carbon atoms, N-arylamino and nitrogen or sulfur heterocyclic of 4-5 carbon atoms;R.sup.3 and one R.sup.2 taken together is a diradical which with the C.dbd.Type: GrantFiled: April 23, 1979Date of Patent: July 29, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: William J. Middleton
-
Patent number: 4214101Abstract: A process for preparing ether carboxylates which comprises contacting an ethoxylated alcohol or alkylphenol or an ethylene oxide/propylene oxide block copolymer, with oxygen, in the presence of a palladium catalyst, at a pH of from 8 to 13 and at a temperature of 50.degree. to 95.degree. C.Type: GrantFiled: April 13, 1978Date of Patent: July 22, 1980Assignee: Kao Soap Co., Ltd.Inventors: Bunji Miya, Akio Kimura
-
Patent number: 4207266Abstract: This invention relates to a novel process for the direct trifluoromethylation of aromatic compounds via carbon tetrachloride and hydrogen fluoride in the presence of strong Bronsted or Lewis acids which give an acidic reaction (increase in concentration of H.sub.2 F.sup.+ ions) in anhydrous hydrogen fluoride.Type: GrantFiled: March 9, 1979Date of Patent: June 10, 1980Assignee: Rohm and Haas CompanyInventor: Thomas R. Opie
-
Patent number: 4198510Abstract: A process for the preparation of carboxylic acids represented by a formula ##STR1## wherein R.sub.1 represents hydrogen atom or a lower alkyl radical, R.sub.2 represents hydrogen atom, lower alkyl or allyl radical and R.sub.3 represents phenyl, substituted phenyl, substituted naphthyl, dibenzofuranyl or substituted biphenyl. Following novel enamine and amidine compounds as intermediates for manufacturing the carboxylic acids and processes for the manufacture of said enamine and amidine compounds ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent the meanings as referred to and R.sub.4 represents dimethylamino, pyrrolidyl, piperidyl or morpholyl.Type: GrantFiled: July 7, 1978Date of Patent: April 15, 1980Assignees: Sanwa Kagaku Kenkyusho Co., Ltd., Takayuki ShioiriInventors: Takayuki Shioiri, Nobutaka Kawai, Masatoshi Ban
-
Patent number: 4194053Abstract: A diester of .alpha.-acetyl-.alpha.'-methyl succinic acid is prepared in improved yield under substantially anhydrous process conditions which minimizes decomposition of that diester by reacting an acetoacetate ester with an .alpha.-halopropionate ester in a solvent containing a nonpolar, aprotic liquid at from about 50.degree. C. to reflux temperature in the presence of a phase transfer agent, a catalytic amount of iodide ion and solid form, substantially anhydrous alkali metal base or basic salt having a high surface area (a size of about 60 mesh or smaller). The resulting diesters can also be used under the stabilizing reaction mixture conditions of this invention as intermediates in processes for making ibuprofen by combining and reacting the .alpha.-acetyl-.alpha.'-methylsuccinate diester with vinyl isobutyl ketone, (or the corresponding Mannich base plus an alkylating agent) and an alkali metal base for a time sufficient to form a reaction mixture containing the .alpha.-methyl-.alpha.'-acetyl-.alpha.Type: GrantFiled: September 1, 1978Date of Patent: March 18, 1980Assignee: The Upjohn CompanyInventor: David R. White
-
Patent number: 4189596Abstract: 2-Aryl-C.sub.2 to C.sub.5 -alkanoic acids and esters thereof are prepared by heating a 2-(2-oxo-3-cyclohexenyl)-alkanoic acid or ester derivative in the presence of a sulfonic acid or a phosphonic acid at 75.degree. C. to 130.degree. C. while providing a means for removing water from the reaction mixture. In the process new butenolide derivative intermediates have been discovered. Alternatively, the 2-aryl-C.sub.2 to C.sub.6 -alkanoic acids can be prepared from the butenolides by forming a mixture of the 2-(2-oxo-3-cyclohexenyl)-alkanoic acid with acetic anhydride in the presence of an acid scavenging base, allowing the mixture to stand for a time sufficient to form an acetate intermediate, heating the resulting mixture to about 75.degree. C. to about 130.degree. C. to form the betenolide intermediates. Thereafter these intermediates can be heated with sulfonic or phosphonic acid as above while removing water to form the 2-aryl-C.sub.2 to C.sub.Type: GrantFiled: May 2, 1977Date of Patent: February 19, 1980Assignee: The Upjohn CompanyInventor: Verlan H. VanRheenen
-
Patent number: 4186270Abstract: Pure 2-(4-isobutylphenyl)propionic acid and related compounds are obtained in good yield by a multi-step process comprising chloromethylation of benzene or an alkylbenzene, conversion of the resulting benzyl chloride to the cyanide, alkylation of that product to the phenylpropionitrile or phenylbutyronitrile, reaction of unreacted benzyl cyanide with an aldehyde to inhibit its hydrolysis, and hydrolysis of the nitrile to the free acid. The products are antiinflammatory, antipyretic, and analgesic drugs.Type: GrantFiled: December 26, 1978Date of Patent: January 29, 1980Assignee: The Dow Chemical CompanyInventors: William Dowd, David H. Naffziger
-
Patent number: 4180672Abstract: Organothiocyclopentanes of the formula ##STR1## wherein E represents >C.dbd.O or ##STR2## in which Z' represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; X represents --S--, --CH.sub.2 --, --CH.dbd.; represents a single or double bond; R' represents a monovalent or divalent organic group containing 1 to 25 carbon atoms; R represents a monovalent organic group containing 1 to 25 carbon atoms; Z represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; and when both E and Z represent a hydroxyl group or a protected hydroxyl group, X represents --S--.Also, 2-organothio-2-cyclopentenones of the formula ##STR3## wherein R and Z are as defined above. The compounds of formula (I) are prepared by reacting 2,3-epoxy-cyclopentanone or its derivatives with mercaptans in the presence of basic compounds.Type: GrantFiled: March 7, 1977Date of Patent: December 25, 1979Assignee: Teijin LimitedInventors: Seizi Kurozumi, Takeshi Toru, Makiko Kobayashi, Yoshinobu Hashimoto
-
Patent number: 4166131Abstract: This invention provides new compounds of formula I, ##STR1## wherein R.sub.1 is lower alkyl,R.sub.2 is hydrogen or lower alkyl,R.sub.3 is hydrogen or lower alkyl,R.sub.4 is hydrogen or lower alkyl,R.sub.5 is hydrogen, chlorine or lower alkyl, and each ofR.sub.6 and R.sub.7 is hydrogen, or, when R.sub.5 is hydrogen, R.sub.6 may also be chlorine or lower alkyl, and R.sub.7 chlorine or lower alkyl,Useful as anti-phlogistic and anti-arthritic agents.Type: GrantFiled: October 24, 1974Date of Patent: August 28, 1979Assignee: Hexachimie Societe AnonymeInventor: Trevor G. Payne
-
Patent number: 4154962Abstract: A new process by which cyclohexanone is treated, in the presence of a suitable acid or a salt of an organic base, with pyruvic acid or with one of its simple derivatives (ester or salt) to give hydratropic acid.Type: GrantFiled: November 1, 1977Date of Patent: May 15, 1979Assignee: Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A.Inventor: Leandro Baiocchi
-
Patent number: 4152351Abstract: Aliphatic unsaturated material or compounds are hydrogenated. Specifically, unsaturated dinitrile, e.g., 5-methyl-4-nonenedinitrile, 2,4-dimethyl-4-octenedinitrile, 2,4-dimethyl-3-octenedinitrile, 2,4,6-trimethyl-3-heptenedinitrile, 5-methylenenonanedinitrile, 2-methyl-4-methyleneoctanedinitrile and 2,6-dimethyl-4-methyleneheptanedinitrile, in a mixture resulting from reaction of isobutylene and acrylonitrile are hydrogenated in presence of a palladium hydrogenation catalyst disposed on an active alumina support also having disposed thereon an adjuvant selected from cerium, thorium, manganese, praseodymium, neodymium and samarium. A specific combination of adjuvants namely cerium together with lanthanum was found to improve the hydrogenation at low levels of cerium.Other aliphatic compounds which can be hydrogenated according to the invention include among others ethylene, 1,3-butadiene, cinnamic acid, 5-methyl-4-nonenedicarboxylic acid, diethyl 5-methylene-nonanedicarboxylate, etc.Type: GrantFiled: August 22, 1977Date of Patent: May 1, 1979Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
-
Patent number: 4144397Abstract: Valuable 2-aryl-propionic acids are prepared by the direct coupling of aryl magnesium bromides with a mixed magnesium halide complex of alpha-bromopropionic acid.Type: GrantFiled: December 19, 1977Date of Patent: March 13, 1979Assignee: Syntex CorporationInventors: Gary J. Matthews, Robert A. Arnold
-
Patent number: 4143229Abstract: Pharmacologically useful alpha (para-alkylphenyl) propionic acids having anti-inflammatory, analgesic and antipyretic activity are prepared from the corresponding 1-haloethyl-para-alkylbenzene by converting same to a diethylacetal via a Grignard reaction, followed by the conversion of said acetal to the corresponding aldehyde by hydrolytic means, converting the said aldehyde to an oxime derivative and hydrolyzing the latter to the desired acid.Type: GrantFiled: April 25, 1977Date of Patent: March 6, 1979Assignee: Alcar S.R.L.Inventor: Massimo Sabbatini
-
Patent number: 4142054Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. A continuous process using a Scheibel column is disclosed. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as an anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: February 27, 1979Assignee: The Upjohn CompanyInventors: Sanjay I. Amin, Jerry A. Walker
-
Patent number: 4135051Abstract: 2-Aryl-C.sub.3 to C.sub.6 -alkanoate esters are prepared economically by reacting an enol ether of an aryl alkyl ketone with a trivalent thallium salt in an organic solvent. The trivalent thallium ions can be regenerated by adding a peracid and a reactive form of manganese, ruthenium, cobalt, iridium, hafnium, osmium or neobium to oxidize monovalent thallium ions to the trivalent state, in a sequential, continuous or stoichiometric procedure. The ester intermediate product is then converted to the corresponding 2-aryl-C.sub.3 - to C.sub.6 -alkanoic acid or salt thereof. The aryl group is selected so the resulting acid product will be a useful compound such as anti-inflammatory, analgesic and anti-pyretic drug or agriculturally useful product. Examples of drug acids which can be made by this process include ibuprofen, flurbiprofen, fenoprofen and naproxen and the like.Type: GrantFiled: June 16, 1977Date of Patent: January 16, 1979Assignee: The Upjohn CompanyInventor: Jerry A. Walker
-
Patent number: 4131747Abstract: A process for preparing an .alpha.-substituted phenylalkanecarboxylic acid, having useful pharmaceutical properties such as analgesic, anti-inflammatory and anti-pyretic properties, from the corresponding ethylidenecyanoacetate by oxidation, hydrolysis, decarboxylation and oxidation.Type: GrantFiled: November 19, 1976Date of Patent: December 26, 1978Assignee: Ono Pharmaceutical Co., Ltd.Inventors: Masayasu Kurono, Masaaki Toda, Haruki Niwa, Syunji Kosuge, Takahumi Iida, Kenichi Narita
-
Patent number: 4119652Abstract: Process for the homogeneous catalytic hydrogenation of olefins, capable of existing as enantiomorphs upon hydrogenation of the olefinic bond, which yields on hydrogenation an optically active mixture. The process comprises the hydrogenation of the olefin in the presence of an optically active coordinated metal hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum.This process is a generalized process for any asymmetric hydrogenation of olefins in which one optical enantiomorph is desired. It is also a generalized process for the selective hydrogenation of olefins in the presence of other reactive groups which are easily hydrogenated. It is especially useful for the preparation of natural products which possess optical activity, such as amino acids, and for products such as flavors, fragrances which may require optical activity for their utilitization.Type: GrantFiled: June 25, 1976Date of Patent: October 10, 1978Assignee: Monsanto CompanyInventors: William S. Knowles, Milton J. Sabacky
-
Patent number: RE29981Abstract: A process for the preparation of organic carboxylic acids which comprises converting a formic acid ester expressed by the general formulaHCOORwherein R stands for a chain or cyclic aliphatic hydrocarbon radical which may have an aliphatic unsaturation, an aryl radical, an aralkyl radical or a heterocyclic radical,At an elevated temperature under raised pressure of carbon monixide to an organic carboxylic acid expressed by the general formulaRCOOHwherein R is as defined above.Type: GrantFiled: July 22, 1977Date of Patent: May 1, 1979Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Nobuo Isogai