Aldehyde Or Ketone Patents (Class 562/459)
  • Patent number: 4334089
    Abstract: Substituted oxocarboxylic acids of the formula I ##STR1## wherein R.sup.1 denotes a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkyl group, a lower alkoxy group or a trifluoromethyl group,R.sup.2 denotes a hydrogen atom or a halogen atom and n denotes an integer from 3 to 8,and their salts display a hypoglycaemic action in warm-blooded animals. Processes for the preparation of the new compounds and of the intermediate products required for their preparation, as well as of the corresponding medicaments are described.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: June 8, 1982
    Assignee: Byk Gulden Lomberg Chemische Fabrik Gesellschaft
    Inventors: Ekkehard Krass, Horst Wolf
  • Patent number: 4334087
    Abstract: A novel process for the manufacture of .alpha.-ketocarboxylic acids which comprises the reaction of oximinohalide with cyanide ion to form oximinonitrile which is reacted with hydroxide ion to form oximinoacid and hydrolysis thereof to the .alpha.-ketoacid.
    Type: Grant
    Filed: September 11, 1980
    Date of Patent: June 8, 1982
    Assignee: Zoecon Corporation
    Inventors: Ted A. Baer, Jeffrey N. Labovitz
  • Patent number: 4323701
    Abstract: The invention relates to a process for the preparation of halogenoindenonecarboxylic acids of the formula ##STR1## in which R.sup.3 is preferably chlorine and R, R.sup.1 and R.sup.2 are, for example, H or -CH.sub.3. If these acids are novel, the corresponding substances are claimed. The invention also relates to corresponding esters of these acids, which contain reactive end groups. The compounds are suitable for the preparation of light-sensitive polymers.
    Type: Grant
    Filed: February 9, 1981
    Date of Patent: April 6, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans Bosshard, Hermann Rempfler, Hans Zweifel
  • Patent number: 4322561
    Abstract: For preparing carbonyl compounds containing certain functional groups, a carbonyl compound is reacted with an unsaturated compound in the presence of a trivalent-manganese initiator and an amine. There is a positive coaction between the trivalent-Mn catalyst and the amine. Typically, 2-methyl-3-butene-2-ol is reacted with acetone in the presence of triethylamine and manganese triacetate (bihydrated) to obtain 2-methyl-heptane-2-ol-3-one. Yields and selectivities are more than satisfactory.
    Type: Grant
    Filed: April 14, 1980
    Date of Patent: March 30, 1982
    Assignee: Anio S.p.A.
    Inventors: Lucio Faggian, Edoardo Platone
  • Patent number: 4307034
    Abstract: 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: Grant
    Filed: September 13, 1979
    Date of Patent: December 22, 1981
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yoshiki Nakayama, Taro Izawa, Yasushi Higuchi, Yutaka Ohishi, Chihiro Yazawa
  • Patent number: 4298530
    Abstract: A process for producing 3-hydroxy-3-methylphthalide or its nuclearly substituted derivative of the following general formula ##STR1## wherein R represents a lower alkyl group, a lower alkoxy group, a lower alkoxycarbonyl group or a carboxyl group, and n is 0 or an integer of 1 to 3,which comprises reacting phthalic anhydride or its nuclearly substituted derivative of the following general formula ##STR2## wherein R and n are as defined, with malonic acid at an elevated temperature in at least one solvent selected from the group consisting of dialkylformamides, dialkylsulfoxides and aliphatic lower carboxylic acids in the presence of, as a catalyst, a salt of an inorganic or organic acid with a metal selected from the group consisting of metals of Groups IA, IIA, IIIB and VIII of the periodic table, manganese, copper and zinc.
    Type: Grant
    Filed: June 2, 1980
    Date of Patent: November 3, 1981
    Assignee: Showa Denko K.K.
    Inventors: Hirokazu Iwasaki, Hideo Takahashi
  • Patent number: 4296244
    Abstract: The present invention provides a novel organic compound, (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid, and a process for the preparation thereof comprising 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, andd. hydrogenating the keto-acid to produce (3-trifluoromethylphenyl)-alpha-hydroxyacetic acid.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: October 20, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4275229
    Abstract: Monoethylenically unsaturated beta-carbonyl-containing carboxyl functional monomers and addition polymers containing them and other monoethylenically unsaturated monomers are disclosed, as are methods of coating substrates with the polymers to provide films of improved water resistance. The monomers are especially stable in the form of a salt with a volatile base, and the removal of the base when a polymer containing the monomer is cured causes decarboxylation, and the removal of the carboxyl groups improves the water resistance.
    Type: Grant
    Filed: February 12, 1979
    Date of Patent: June 23, 1981
    Assignee: DeSoto, Inc.
    Inventors: Stamatios G. Mylonakis, Anthony J. Tortorello
  • Patent number: 4273785
    Abstract: Novel 4-monoalkylamino-benzaldehydes, 4-mono-alkylamino-alkanophenones, and 4-monoalkylamino-benzophenones, and derivatives and salts thereof, are disclosed which are useful as anti-atherosclerotic agents.
    Type: Grant
    Filed: September 27, 1977
    Date of Patent: June 16, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4268687
    Abstract: 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: Grant
    Filed: November 7, 1979
    Date of Patent: May 19, 1981
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4263445
    Abstract: This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
    Type: Grant
    Filed: April 28, 1978
    Date of Patent: April 21, 1981
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4263212
    Abstract: The present invention relates to a process for the preparation of aromatic or furyl substituted olefins, which comprises reacting an olefinic compound with an aromatic compound or furan compound in the presence of carbon monoxide by using a rhodium carbonyl complex as a catalyst to form a corresponding aromatic or furyl substituted olefin.
    Type: Grant
    Filed: February 14, 1980
    Date of Patent: April 21, 1981
    Assignee: Rikagaku Kenkyusho
    Inventors: Pangbu Hong, Hiroshi Yamazaki
  • Patent number: 4259352
    Abstract: This disclosure describes novel 4-[(cycloalkyl or cycloalkenyl substituted)amino, alkylamino or alkenylamino]phenyl compounds, salts and derivatives of these such as cycloalkylamino, cycloalkenylamino, cycloalkyl-alkylamino, cycloalkyl-alkenylamino, cycloalkenyl-alkylamino, and cycloalkyl-cycloalkylamino phenyl compounds and derivatives and suitable salts of these; these compounds are useful as hypolipidemic and antiatherosclerotic agents.
    Type: Grant
    Filed: February 1, 1979
    Date of Patent: March 31, 1981
    Assignee: American Cyanamid Company
    Inventor: Robert G. Shepherd
  • Patent number: 4259250
    Abstract: The present invention provides novel thromboxane analogs and intermediates. Particularly, the present invention provides novel 11a-homo-PG intermediates for preparing 11a-methano TXA.sub.2 compounds.
    Type: Grant
    Filed: January 28, 1980
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4254274
    Abstract: Novel 4-(2-oxo-1-cycloalkylidenemethyl)phenylacetic acid derivatives and non-toxic pharmaceutically acceptable salts thereof are useful as anti-inflammatory agents.The compounds may be prepared by reacting a p-formylphenylacetic acid ester derivative with an enamine of cycloalkanone and hydrolyzing the resulting product, or with a cycloalkanone in the presence of a base.
    Type: Grant
    Filed: August 1, 1978
    Date of Patent: March 3, 1981
    Assignee: Sankyo Company Limited
    Inventors: Atsusuke Terada, Shigeru Tanaka, Eiichi Misaka
  • Patent number: 4243677
    Abstract: Perhaloalkylvinylcyclopropanecarboxylates having the general formula ##STR1## are disclosed wherein one of Y and Z is a perhaloalkyl group. Compounds in which R is hydroxy, halogen or lower alkoxy are novel intermediates for preparation of insecticidal esters in which R is --OR.sup.1 where R.sup.1 is a wide variety of alcohol residues. The insecticidal efficacy and preparation of the compounds and intermediates therefor are described and exemplified.
    Type: Grant
    Filed: July 30, 1979
    Date of Patent: January 6, 1981
    Assignee: FMC Corporation
    Inventor: John F. Engel
  • Patent number: 4238413
    Abstract: 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: Grant
    Filed: November 7, 1979
    Date of Patent: December 9, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4234739
    Abstract: Glyoxylic acids or derivatives thereof are prepared by reacting an acyl nitrile compound with concentrated sulfuric acid in the presence of halide anion to form a first reaction product and then further reacting the first reaction product with a compound of the general formula ROH to form the desired glyoxylic acid or glyoxylic acid derivative.
    Type: Grant
    Filed: December 5, 1978
    Date of Patent: November 18, 1980
    Assignee: Stauffer Chemical Company
    Inventors: James M. Photis, Fred S. Eiseman, Sidney M. Gister
  • Patent number: 4227015
    Abstract: Aryl substituted diketones and keto-esters, useful as antiviral agents and insecticides, are prepared by reacting an arylalkyl or arylalkenyl iodide with a metal salt of the appropriate diketone or keto-ester. The intermediate iodides are prepared by condensing a methyl cyclopropyl ketone with an aromatic aldehyde to give an arylvinyl cyclopropyl ketone, reducing the latter to an arylethyl cyclopropyl carbinol or arylvinyl cyclopropyl carbinol, treating the carbinol with phosphorus tribromide and then with zinc bromide to give an arylalkyl or arylalkenyl bromide, and then replacing the bromine atom by iodine.
    Type: Grant
    Filed: February 14, 1979
    Date of Patent: October 7, 1980
    Assignee: Sterling Drug Inc.
    Inventor: Joseph C. Collins
  • Patent number: 4220753
    Abstract: Alkyl alkoxymethylbenzoates and essentially linear polyester ethers and copolyester ethers therefrom.
    Type: Grant
    Filed: December 18, 1978
    Date of Patent: September 2, 1980
    Assignee: Standard Oil Company (Indiana)
    Inventors: Steven A. Cerefice, Edward E. Paschke
  • Patent number: 4218378
    Abstract: The present invention provides novel 11a-methano-TXA compounds and intermediates and processs for their preparation. Further provided are methods for using these novel TXA analogs as inhibitors of thromboxane synthetase, rendering these analogs useful for a variety of pharmacological purposes. These pharmacological uses include anti-inflammatory, anti-thromobitc, and anti-asthma indications.
    Type: Grant
    Filed: May 1, 1979
    Date of Patent: August 19, 1980
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4218380
    Abstract: Novel process for the preparation of an arylglyoxylic acid compound, e.g., phenylglyoxylic acid, which comprises oxidizing an .alpha.-hydroxyarylacetic acid, e.g., mandelic acid, of the formula ##STR1## in which m is 1, 2 or 3,each R individually is hydrogen, alkyl, cycloalkyl,aryl, aralkyl, alkoxy, cycloakoxy, aryloxy, hydroxyl,halogen, aminoalkyl or carboxyl,with the proviso thattwo R's together can represent the methylenedioxygroup or a fused-on, optionally heterocyclic andoptionally substituted ring,with oxygen or a gas containing molecular oxygen in aqueous alkaline medium in the presence of a catalyst comprising a platinum-group metal in the presence as an activator of at least one of lead, a lead compound, bismuth and a bismuth compound at a temperature of up to the boiling point of the resulting reaction mixture.
    Type: Grant
    Filed: May 11, 1979
    Date of Patent: August 19, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Fiege, Karlfried Wedemeyer, Kurt Bauer, Reiner Molleken
  • Patent number: 4215222
    Abstract: Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, for example ##STR1## or (2) a 9-deoxy-6,9-epoxy feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
    Type: Grant
    Filed: November 9, 1978
    Date of Patent: July 29, 1980
    Assignee: The Upjohn Company
    Inventor: Udo F. Axen
  • Patent number: 4206152
    Abstract: The present invention provides a process for the production of unsubstituted or substituted o-phthalaldehydes by hydrolysis of .alpha.,.alpha., .alpha.',.alpha.'-tetrahalogeno-o-xylenes with a carboxylate in an aqueous medium in the presence of a phase transfer catalyst and an organic base.
    Type: Grant
    Filed: December 21, 1978
    Date of Patent: June 3, 1980
    Assignee: Ciba-Geigy Corporation
    Inventor: Jacques Gosteli
  • Patent number: 4181736
    Abstract: This invention relates to phenylacetic acid derivatives having the formula: ##STR1## in which A represents a grouping ##STR2## R, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, represent each hydrogen or an alkyl group, and represents a single or double carbon-carbon bond; and their salts with inorganic and organic bases. Said compounds possess anti-inflammatory and analgesic activities that make them therapeutically useful, in particular for the treatment of rheumatic diseases and of local inflammations.
    Type: Grant
    Filed: November 21, 1978
    Date of Patent: January 1, 1980
    Assignee: Laboratoires Jacques Logeais
    Inventor: Jacques G. Maillard
  • Patent number: 4174352
    Abstract: A process for preparing an allylic or an aromatic aldehyde, such as acrolein or benzaldehyde, the process comprising contacting in a basic, liquid, biphasic mixture and at reactive conditions an allylic halide or a halomethylated aromatic, such as allyl or benzyl chloride, with a divalent chromate ion, is improved by contacting the allylic halide or halomethylated aromatic with the divalent chromate ion in the presence of a catalytic amount of a quaternary ammonium and/or phosphonium salt, such as tetra-n-butylammonium chloride. The improved process is faster, cleaner and more complete than the process of the prior art.
    Type: Grant
    Filed: May 8, 1978
    Date of Patent: November 13, 1979
    Assignee: The Dow Chemical Company
    Inventors: Thomas H. Fisher, William Dowd
  • Patent number: 4166131
    Abstract: 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: Grant
    Filed: October 24, 1974
    Date of Patent: August 28, 1979
    Assignee: Hexachimie Societe Anonyme
    Inventor: Trevor G. Payne
  • Patent number: 4161538
    Abstract: 4-(2-Oxo- or hydroxyimino-cycloalkan-1-ylmethyl)phenylacetic acid derivative and nontoxic pharmaceutically acceptable salt thereof are useful as an anti-inflammatory agent. The above 2-oxo-compound may be prepared by (a) hydrolyzing and decarboxylating 4-(1-alkoxycarbonyl-2-oxocycloalkan-1-ylmethyl)phenylacetic acid ester derivative or (b) reacting p-halomethylphenylacetic acid ester derivative with an enamine of cycloalkanone and hydrolyzing the resulting product. And further, the above 2-hydroxyimino-compound may be prepared by (c) reacting 4-(2-oxocycloalkan-1-ylmethyl)phenylacetic acid derivative (the product of process (a) or (b)) with hydroxylamine or (d) reacting a dilithium salt of cycloalkanone oxime with p-halomethyl- or p-sulfonyloxymethyl-phenylacetic acid ester derivative and hydrolyzing the resulting product.
    Type: Grant
    Filed: March 10, 1978
    Date of Patent: July 17, 1979
    Assignee: Sankyo Company Limited
    Inventors: Atsusuke Terada, Kazuyuki Wachi, Eiichi Misaka
  • Patent number: 4152456
    Abstract: Tropone derivatives substituted with an amino-, thio- or oxy-derivative of oxalic acid or acetic acid are disclosed. In addition, the tropone nucleus can be optionally further substituted. The foregoing compounds are useful for preventing or treating allergic conditions in a mammal. Methods for the preparation and use of the compounds are disclosed.
    Type: Grant
    Filed: October 7, 1977
    Date of Patent: May 1, 1979
    Assignee: Ayerst, McKenna and Harrison Limited
    Inventors: Jehan F. Bagli, Tibor Bogri
  • Patent number: 4145362
    Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.
    Type: Grant
    Filed: May 10, 1977
    Date of Patent: March 20, 1979
    Assignee: S.A. P R B en Neerlandais PRB N.V.
    Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
  • Patent number: 4139717
    Abstract: 1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific .alpha.,.beta.-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.
    Type: Grant
    Filed: January 4, 1977
    Date of Patent: February 13, 1979
    Assignee: Teijin Limited
    Inventors: Seizi Kurozumi, Takeshi Toru, Toshio Tanaka, Shuzi Miura, Makiko Kobayashi, Sachio Ishimoto
  • Patent number: 4131747
    Abstract: 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: Grant
    Filed: November 19, 1976
    Date of Patent: December 26, 1978
    Assignee: Ono Pharmaceutical Co., Ltd.
    Inventors: Masayasu Kurono, Masaaki Toda, Haruki Niwa, Syunji Kosuge, Takahumi Iida, Kenichi Narita
  • Patent number: 4113742
    Abstract: A process for the preparation of tetrahydro-alpha-pyrones comprises preparing the alkyl ester of a 5-oxo alkanoic acid from a 4-oxo alkane carbonitrile, obtained in a first stage by the action of benzyl cyanide on the corresponding alkenone, and then saponifying the obtained ester, followed by hydrogenation and cyclization.
    Type: Grant
    Filed: June 14, 1976
    Date of Patent: September 12, 1978
    Assignee: Union Chimique Continentale-U.C.C.
    Inventor: Pierre Simon
  • Patent number: 4113767
    Abstract: 6-Tert.-butyl-3-mercapto-4-amino-1,2,4-triazin-5(4H)-one is prepared by reacting pinacolone with a sulfur chloride at 0.degree. to 80.degree. C, optionally reacting the mixture with an aqueous amine solution, hydrolyzing the resulting product with an alkali metal hydroxide, heating the resulting mixture from 2 to 10 hours at 80.degree. to 150.degree. C, liberating a 3,3-dimethyl-2-oxo-butyric acid by acidifying with a mineral acid and reacting an aqueous solution of said 3,3-dimethyl-2-oxo-butyric acid with thiocarbohydrazide to yield the desired product.
    Type: Grant
    Filed: December 15, 1975
    Date of Patent: September 12, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventor: Walter Merz