Additional Ring Containing Patents (Class 568/807)
  • Patent number: 4410716
    Abstract: Novel compounds, dibenzo[a,d]cycloheptene derivatives, of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a halogen atom or a lower alkyl group, R.sub.2 and R.sub.3 each represent a hydrogen atom or a lower alkyl group, and Z represents a group of the formula ##STR2## These novel compounds are useful as non-steroidal anti-inflammatory agents free from gastrointestinal lesions. The compounds of formula (I) can be prepared, for example, by cyclizing a compound of the general formula ##STR3## wherein R.sub.1 and R.sub.2 are as defined above, X represents a hydroxyl group or a halogen atom, one Y represents a group of the formula --CH.sub.2 COX and the other Y represents a hydrogen atom; optionally hydrolyzing the cyclized product; and optionally esterifying the product, and/or etherifying its enol group.
    Type: Grant
    Filed: September 24, 1980
    Date of Patent: October 18, 1983
    Assignee: Toa Eiyo Kagaku Kogyo Co. Ltd.
    Inventors: Tetsutaro Hayasaka, Kuniro Saito, Sen-ichi Narita, Takao Goto, Shin-ichi Yamada, Teruo Saito, Kazuyoshi Okutani
  • Patent number: 4402973
    Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: May 21, 1981
    Date of Patent: September 6, 1983
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4393079
    Abstract: Anti-inflammatory compositions are prepared which comprise a therapeutically effective amount of a compound of the formula ##STR1## wherein X is CO or CHOH; Y is CO; the dotted line represents a double bond which is present or absent; R.sub.1 is hydrogen or methyl; R.sub.2 is hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxyl, hydroxyl, acetoxyl, nitro or amino; R.sub.3 is alkyl of 3 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkenyl of 5 to 8 carbon atoms or phenyl unsubstituted or substituted by 1 or 2 substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, methoxyl, ethoxyl, benzyloyl, hydroxyl, acetoxyl, trifluoromethyl, nitro, amino, acetyl, methylthiol, methylsulphonyl, methylamino and dimethylamino. Compounds of formula I above are also novel.
    Type: Grant
    Filed: December 15, 1976
    Date of Patent: July 12, 1983
    Assignee: Beecham Group Limited
    Inventors: William G. Cole, Alexander C. Goudie, Carl J. Rose
  • Patent number: 4329518
    Abstract: [1,1'-Biphenyl]-3-ylmethyl pyrethroid esters, as well as processes, uses, and intermediates thereto, are disclosed. The [1,1'-biphenyl]-3-ylmethyl pyrethroid esters control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: October 2, 1980
    Date of Patent: May 11, 1982
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4326055
    Abstract: This invention is directed to 5,6,7,8-tetrahydro-naphthyl or indanyl stilbene derivatives which are useful as tumor inhibiting agents, in the treatment of neoplasms, dermatological conditions and rheumatic illnesses.
    Type: Grant
    Filed: December 15, 1978
    Date of Patent: April 20, 1982
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Peter Loeliger
  • Patent number: 4322567
    Abstract: In a process for producing an aromatic alcohol by catalytic hydrogenation of at least one tertiary peroxide selected from the group consisting of tertiary aromatic hydroperoxides and tertiary aromatic peroxides in the presence of a palladium catalyst in a lower aliphatic alcohol solvent to form the corresponding alcohol; the improvement wherein said catalyst has a palladium metal surface area, determined by the CO chemisorption method, of up to about 200 m.sup.2 /g.multidot.Pd.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: March 30, 1982
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Fujihisa Matsunaga, Norio Ohno, Hirohiko Nambu
  • Patent number: 4322442
    Abstract: 1-Halo-1-propyn-3-ols of the formula ##STR1## in which R is optionally substituted phenyl, pyridyl, furyl, thienyl or pyrazolyl,R' is optionally substituted phenyl, andX is halogen,which possess fungicidal properties.
    Type: Grant
    Filed: September 8, 1980
    Date of Patent: March 30, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Jager, Erich Klauke, Wilhelm Brandes, Paul-Ernst Frohberger
  • Patent number: 4317918
    Abstract: An alcohol is produced in a high selectivity with a good yield from the corresponding carboxylic acid by reducing the latter with hydrogen in the presence of a rhenium catalyst in the coexistence of an organic base. An arylacetic acid, which is included in the starting carboxylic acid, can be produced in an excellent yield from the corresponding aryl aldehyde by reacting the latter with carbon monoxide and water in the presence of rhodium or its compound and hydrogen iodide.
    Type: Grant
    Filed: November 3, 1980
    Date of Patent: March 2, 1982
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tetsuo Takano, Gohu Suzukamo, Masaru Ishino, Kiyoshi Ikimi
  • Patent number: 4317941
    Abstract: The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharmacological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.
    Type: Grant
    Filed: August 11, 1978
    Date of Patent: March 2, 1982
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4310700
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: January 12, 1982
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4306076
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet anti-aggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 15, 1981
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4306075
    Abstract: The present specification provides novel analogs of carbacyclin (CBA.sub.2), 6a-carba-prostacyclin (6a-carba-PGI.sub.2), which have pronounced prostacyclin-like pharmacological activity, e.g., as platelet antiaggregatory agents. Specifically the novel chemical analogs of CBA.sub.2 are those substituted by fluoro (C-5), alkyl (C-9), interphenylene (C-5), and methano (C-6a,9). Further provided are benzindene analogs of CBA.sub.2 and substituted forms thereof, i.e., 9-deoxy-2',9-methano (or 2',9-metheno)-3-oxa-4,5,6-trinor-3,7-(1',3'-interphenylene)-PGF.sub.1 compounds. Also provided are a variety of novel chemical intermediates, e.g., substituted bicyclo[3.3.0]octane intermediates, and chemical process utilizing such intermediates which are useful in the preparation of the novel CBA.sub.2 analogs.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: December 15, 1981
    Assignee: The Upjohn Company
    Inventor: Paul A. Aristoff
  • Patent number: 4304733
    Abstract: Novel alcohols of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of carbamoyl and R.sub.1 ' and R.sub.2 ', R.sub.1 ' and R.sub.2 ' are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 6 carbon atoms, aryl of 6 to 10 carbon atoms, arylalkyl of 7 to 13 carbon atoms, alkoxycarbonyl of 2 to 5 carbon atoms and --CN and R.sub.3 and R.sub.3 ' are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 3 carbon atoms in the S form, R form or racemic mixtures thereof whose esters with cyclopropane carboxylic acids have an elevated insecticidal activity and their preparation.
    Type: Grant
    Filed: April 17, 1980
    Date of Patent: December 8, 1981
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4301166
    Abstract: The invention relates to hydroxyethyl-azole compounds and methods for their preparation. Also included in the invention are compositions containing said hydroxyethyl-azole compounds and methods for the use of said compounds and compositions as antimycotic agents.
    Type: Grant
    Filed: November 9, 1979
    Date of Patent: November 17, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erik Regel, Karl H. Buchel, Ingo Haller, Manfred Plempel
  • Patent number: 4291175
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 22, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4291174
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 22, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4289910
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 15, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288640
    Abstract: Process for carrying out exothermic reactions between a gas and a liquid in the presence of a solid catalyst by passing the gas and the liquid cocurrently through a packed reaction vessel, preferably of elongated shape, wherein the gas and liquid pass through the packed reaction vessel in transition flow.
    Type: Grant
    Filed: July 22, 1976
    Date of Patent: September 8, 1981
    Assignee: BASF Aktiengesellschaft
    Inventors: Ludwig Schuster, Paul Raff, Herwig Hoffmann, Rolf Schneider, Erich Flickinger
  • Patent number: 4288633
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288630
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation enhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4288629
    Abstract: Prostaglandin analogs are disclosed that have the .alpha.-chain terminating with the group --CH(OR')OR" wherein R' and R" are the same or different and are hydrogen, C.sub.1 to C.sub.4 alkanoyl or optionally substituted benzoyl, the substituents selected from the group C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, halo and trifluoromethyl. These compounds are useful as hypotensive agents, gastric secretory and platelet aggregation inhibitors and bronchodilators.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: September 8, 1981
    Assignee: American Cyanamid Company
    Inventors: Allan Wissner, Middleton B. Floyd, Jr.
  • Patent number: 4275071
    Abstract: Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: ##STR1## In the formula, R.sub.4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO.sub.2, CH.sub.3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH.sub.2, NO.sub.2, CH.sub.3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C.sub.1 -C.sub.6 alkyl or C.sub.1 C.sub.6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl,n=0, 1 or 2 and(a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R.sub.1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R.sub.2 and R.sub.3 =H the other of R.sub.2 and R.sub.3 =H, OH, benzoyloxy, C.sub.2 -C.sub.7 alkanoyloxy, N-(C.sub.1 -C.sub.6 alkyl)-carbamoyloxy, N,N-[di-(C.sub.1 C.sub.6)alkyl]-carbamoyloxy, but if R.sub.2 =R.sub.3 =H then R=R.sub.1 =H, or(b) R=H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.1 =H, C.sub.1 -C.sub.6 alkyl, phenyl R.sub.2 +R.sub.
    Type: Grant
    Filed: July 10, 1979
    Date of Patent: June 23, 1981
    Assignee: Recordati S.A.
    Inventors: Dante Nardi, Alberto Tajano, Maria J. Magistretti
  • Patent number: 4273933
    Abstract: A modified nickel catalyst used for stereo-differentiating reduction of carbonyl compounds is provided. The modified nickel catalyst is prepared by soaking a nickel catalyst in an aqueous modifying medium having dissolved therein at least one inorganic salt, such as sodium bromide or sodium chloride, and at least one optically active substance, such as optically active hydroxy acid. The modified nickel catalyst exhibits enhanced activity for stereo-differentiating reduction and causes little or no side reactions, and thus, brings about an extremely high yield of the reaction product.
    Type: Grant
    Filed: April 25, 1979
    Date of Patent: June 16, 1981
    Assignee: Kawaken Fine Chemicals Co., Ltd.
    Inventors: Tadao Harada, Yoshiharu Izumi, Shinichiro Komatsu
  • Patent number: 4271091
    Abstract: Cyclohexanone and/or cyclohexanol can be oxidized in the vapor phase to phenol by contacting the cyclohexanone and/or cyclohexanol with a suitable oxidation catalyst in the presence of molecular oxygen. Suitable catalysts are solids comprising Mo, W, Sb and/or V oxides or complexes thereof. The catalysts may be promoted with additional elements.
    Type: Grant
    Filed: June 17, 1978
    Date of Patent: June 2, 1981
    Assignee: Standard Oil Company
    Inventors: Robert K. Grasselli, Dev D. Suresh
  • Patent number: 4267388
    Abstract: There is disclosed a novel process for preparing anti-inflammatory ethynylbenzene derivatives represented by the general formula I: ##STR1## wherein Y is hydrogen, halogen or loweralkyl of 1 to 3 carbon atoms; R represents a ring having the structure: ##STR2## wherein x is 1 to 3, or a ring of the structure: ##STR3## wherein Y' is hydrogen, halogen, loweralkyl of 1 to 3 carbon atoms and loweralkoxy of 1 to 3 carbon atoms; Y" is hydrogen or halogen; and Y"' is hydrogen or halogen, provided Y, Y', Y" and Y"' are not all hydrogen at the same time, by reacting a benzyl alcohol of formula V: ##STR4## with a sulfonyl chloride, reducing the sulfonate VI of the formula: ##STR5## and dehydrohalogenating the formed .beta.
    Type: Grant
    Filed: July 12, 1979
    Date of Patent: May 12, 1981
    Assignee: William H. Rorer, Inc.
    Inventors: Paul R. Darkes, Henry F. Campbell, George H. Douglas
  • Patent number: 4263457
    Abstract: A process for producing a halobiphenyl derivative represented by the following formula (I) comprises dehydrogenating a cyclohexylhalobenzene represented by the following formula (II) under such conditions that substantially no dehalogenation occurs. ##STR1## wherein X represents a halogen atom, and each of R.sup.1 and R.sup.2 independently represents a group represented by the formula ##STR2## wherein A represents carboxyl or an alkoxycarbonyl group and R represents a hydrogen atom or a lower alkyl group; an alkylcarbonyl; alkenyl; alkynyl; alkyl; aryl; arylcarbonyl; hydroxyalkyl; cyanoalkyl or cyanoalkenyl group.
    Type: Grant
    Filed: August 17, 1979
    Date of Patent: April 21, 1981
    Assignee: Mitsubishi Petrochemical Company, Ltd.
    Inventors: Makoto Takeda, Eiji Taniyama, Yuji Ozawa, Makoto Imanari, Kunimasa Takahashi, Hiroshi Iwane
  • Patent number: 4259528
    Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-PG.sub.1 compounds, methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4259529
    Abstract: The present invention provides novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-13,14-dihydro-PG.sub.1 compounds methods for their preparation and pharmacological use for the induction of prostaglandin-like effect.
    Type: Grant
    Filed: October 17, 1979
    Date of Patent: March 31, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4243611
    Abstract: Prostaglandin derivatives having a 19,20-didehydro, a 19-hydroxy, or a 19-keto feature are disclosed, including processes for preparing them and the appropriate intermediates.A typical 19-hydroxy compound of this invention is 19-hydroxy-19-methyl-PGF.sub.2.alpha.
    Type: Grant
    Filed: April 2, 1979
    Date of Patent: January 6, 1981
    Assignee: The Upjohn Company
    Inventor: John C. Sih
  • Patent number: 4224244
    Abstract: Novel 9-phenyl 5,6-dimethyl-nona-2,4,6,8-tetraenoic acid, tetraenal or tetraenol derivatives useful as anti-tumor agents.
    Type: Grant
    Filed: May 9, 1979
    Date of Patent: September 23, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Werner Bollag, Rudolf Ruegg, Gottlieb Ryser
  • Patent number: 4223172
    Abstract: Bromoarylacetylenes such as m-bromophenylacetylene and certain precursors to such bromoarylacetylene are prepared by reacting an aryldibromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence. The bromoarylacetylenes can be reacted with a substituted terminal acetylene compound as defined using the same catalyst system as defined to produce the corresponding aryldihydroxy substituted acetylenes. Certain bromophenylhydroxy substituted acetylenes are claimed as new compositions.
    Type: Grant
    Filed: December 7, 1978
    Date of Patent: September 16, 1980
    Assignee: Gulf Research & Development Company
    Inventors: Edward T. Sabourin, Charles M. Selwitz
  • Patent number: 4214004
    Abstract: Substituted [1,1'-biphenyl]-3-ylmethyl 3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates, as well as processes, uses, and intermediates thereto, are disclosed. The substituted [1,1'-biphenyl]-3-ylmethyl 3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates control a broad spectrum of insects as well as acarids.
    Type: Grant
    Filed: December 4, 1978
    Date of Patent: July 22, 1980
    Assignee: FMC Corporation
    Inventor: Ernest L. Plummer
  • Patent number: 4212999
    Abstract: The present invention relates to a novel organic compound, 1-phenyl-3-(3-trifluoromethylphenyl)-1,2-propane diol. This compound may be produced by:(a). condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,(b). epoxidation of the substituted chalcone to produce the corresponding epoxide,(c). converting the epoxide to a chlorohydrin, and(d). catalytic hydrogenolysis of the chlorohydrin to produce a diol, 1-phenyl-3-(3-trifluoromethylphenyl)-1,2-propan-diol.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: July 15, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4212998
    Abstract: The present invention relates to a novel organic compound, 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanol. This compound may be produced by:a. condensing 3-trifluoromethylbenzaldehyde with acetophenone under basic conditions to form a substituted chalcone,b. epoxidation of the substituted chalcone to produce the corresponding epoxide,c. converting the epoxide to a chlorohydrin, andd. catalytic hydrogenolysis of the chlorohydrin to produce a diol and subsequently converting the diol into the corresponding alcohol, 1-phenyl-3-(3-trifluoromethylphenyl)-2-propanol.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: July 15, 1980
    Assignee: Hooker Chemicals & Plastics Corp.
    Inventors: David Y. Tang, Arthur M. Foster
  • Patent number: 4211666
    Abstract: Novel compounds, 4-alkyl-cyclohexenes having at the 1-position thereof p-cyanophenyl group or 4'-cyano-4-biphenylyl group, expressed by the general formula ##STR1## wherein R represents a straight alkyl group having 1.about.9 carbon atoms and n represents 1 or 2; methods for producing the same; and nematic liquid crystal (L.C.) compositions comprising at least one member selected from the group consisting of said compounds, are provided.Said compounds having a cyclohexene ring have a lower viscosity than conventional L.C. compounds, and have effectivenesses of short response time when applied to L.C. display apparatus; superior compatibility with other L.C. compounds to form convenient L.C. mixture; and no need of separating cis- and trans-forms in the midway step of the preparation as in the prior art.
    Type: Grant
    Filed: November 14, 1978
    Date of Patent: July 8, 1980
    Assignee: Chisso Corporation
    Inventors: Takashi Inukai, Hiromichi Inoue, Hideo Sato
  • Patent number: 4211884
    Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxylic is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes 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: February 24, 1978
    Date of Patent: July 8, 1980
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4210610
    Abstract: Chloroarylacetylenes such as m-chlorophenylacetylene and certain precursors to such chloroarylacetylene are prepared by reacting a chloroarylbromide with a substituted terminal acetylene compound containing at least three carbon atoms and a hydroxy group on the carbon atom adjacent to the acetylene group in the presence of a dialkyl or trialkyl amine solvent and a catalyst system consisting of a palladium complex containing two halogen moieties and two tri-substituted phosphine moieties. Additional triphenylphosphine can be added. A cuprous iodide promoter is also employed in the reaction sequence.
    Type: Grant
    Filed: December 7, 1978
    Date of Patent: July 1, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Edward T. Sabourin, Charles M. Selwitz
  • Patent number: 4208538
    Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes 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: January 3, 1978
    Date of Patent: June 17, 1980
    Assignee: The Upjohn Company
    Inventor: Norman A. Nelson
  • Patent number: 4207422
    Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes 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: February 24, 1978
    Date of Patent: June 10, 1980
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4206311
    Abstract: This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes 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: February 24, 1978
    Date of Patent: June 3, 1980
    Assignee: The Upjohn Company
    Inventor: Herman W. Smith
  • Patent number: 4181810
    Abstract: A process for the preparation of a propane-1,3-diol, disubstituted in the 2-position, which comprises contacting an ethanal disubstituted in the 2-position, which ethanal has the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and denote optionally substituted alkyl, cycloalkyl, aralkyl or aryl radicals or an optionally substituted heterocyclic radical, or together denote an optionally substituted divalent hydrocarbon radical with formaldehyde in the presence of an acid ion exchanger and thereafter contacting the resultant reaction product with hydrogen under hydrogenation conditions.
    Type: Grant
    Filed: November 16, 1977
    Date of Patent: January 1, 1980
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Helmut Schwarz, Oskar Weissel
  • Patent number: 4178300
    Abstract: A novel process is described for the preparation of novel organic solutions of organooxy magnesium compounds of low viscosity, which solutions are formed in the presence of at least 5 mol % based on the magnesium compound of an organooxy compound of a transition metal of Groups IV through VI of the Periodic Table.
    Type: Grant
    Filed: October 31, 1978
    Date of Patent: December 11, 1979
    Assignee: Stamicarbon, B.V.
    Inventor: Cornelis E. P. V. van den Berg
  • Patent number: 4178297
    Abstract: This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominately cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
    Type: Grant
    Filed: November 16, 1978
    Date of Patent: December 11, 1979
    Assignee: Texas Alkyls, Inc.
    Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin
  • Patent number: 4163865
    Abstract: An improvement in a process for the preparation of a pinacol of the formula ##STR1## wherein R.sup.1 and R.sup.2 are identical or different and represent optionally substituted aliphatic, cycloaliphatic, araliphatic or an aromatic hydrocarbon radical by reducing a ketone of the formula ##STR2## wherein R.sup.1 and R.sup.2 have the abovementioned meanings with a base metal, the improvement comprising carrying out the reduction in the presence of an organic halogen compound and in the presence of a phosphoric acid amide, phosphoric acid ester and/or carboxylic acid amide.
    Type: Grant
    Filed: April 3, 1978
    Date of Patent: August 7, 1979
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Wolfers, Hans Rudolph, Hans-Jurgen Rosenkranz
  • Patent number: 4163758
    Abstract: 2-Nitroethylcyclopentane compounds represented by the formula (I) ##STR1## wherein X represents a ##STR2## R and R.sup.1 each represents a hydrogen atom or a protective group for a hydroxy group, R.sup.2 represents an unsubstituted or substituted alkyl group having 1 to 8 carbon atoms and R.sup.5 represents a hydrogen atom or an alkyl group havng 1 to 4 carbon atoms, which are useful as intermediates for the synthesis of prostaglandin compounds, and a process for preparing the 2-nitroethylcyclopentane compounds of the formula (I).
    Type: Grant
    Filed: September 6, 1978
    Date of Patent: August 7, 1979
    Assignee: Sagami Chemical Research Center
    Inventors: Kiyosi Kondo, Daiei Tunemoto, Teruo Umemoto
  • Patent number: 4154697
    Abstract: Novel liquid crystals have the formula ##STR1## wherein two of the rings A, B and C are aromatic and the third is a trans-1,4-disubstituted cyclohexane ring and R is alkyl or alkoxy each of 1 - 12 C-atoms. These compounds are particularly useful as additional components in liquid crystal dielectrics whereby the clear point of the dielectric is raised and the viscosity thereof is not deleteriously affected.
    Type: Grant
    Filed: January 11, 1978
    Date of Patent: May 15, 1979
    Assignee: Merck Patent Gesellschaft mit beschraenkter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause, Ludwig Pohl
  • Patent number: 4151302
    Abstract: Compounds of the formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and are F, Cl or Br;Q is --CH(CH.sub.3)--CH.sub.2 --, --C(OH)(CH.sub.3)--CH.sub.2 -- or --C(CH.sub.3).dbd.CH--;Y is COOH, COOR.sup.3, CH.sub.2 OH or CH.sub.2 OAc;N is 0 or 1;R.sup.3 is alkyl or aryl of up to 8 carbon atoms or C.sub.6 H.sub.4 NHCOCH.sub.3 ; andAc is acyl of 1-8 carbon atoms;And physiologically acceptable salts thereof, are anti-inflammatory agents, which can be made from compounds of the formula Z--X, wherein Z is ##STR2## X can be converted to --Q--Y.
    Type: Grant
    Filed: August 19, 1977
    Date of Patent: April 24, 1979
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Joachim Gante, Hans-Adolf Kurmeier, Dieter Orth, Erich Schacht, Albrecht Wild
  • Patent number: 4145561
    Abstract: The present invention relates to novel 2-decarboxy-2-hydroxymethyl-9-deoxy-9-methylene-16-phenyl-PGF compounds. These compounds are useful pharmacological agents, and are useful for the same purposes as the corresponding PGE-type compounds.
    Type: Grant
    Filed: July 12, 1978
    Date of Patent: March 20, 1979
    Assignee: The Upjohn Company
    Inventor: Gordon L. Bundy
  • Patent number: 4140863
    Abstract: The present invention relates to certain 9,11-dideoxy-PGF-type compounds wherein the C-9 and C-11 carbon atoms are substituted by halogen. In particular, 9,11-chloro-, 9,11-bromo-, and 9,11-iodo-9,11-dideoxy-PGF compounds are disclosed.These compounds are particularly useful for numerous pharmacological purposes, based on their ability to stimulate mammalian smooth muscle tissue.
    Type: Grant
    Filed: June 17, 1977
    Date of Patent: February 20, 1979
    Assignee: The Upjohn Company
    Inventor: Roy A. Johnson
  • Patent number: 4133815
    Abstract: This invention relates to the preparation of unsaturated alcohols useful as flavor and fragrance compounds. More specifically, this invention relates to the preparation of predominantly cis-unsaturated alcohols by reacting a cis-1-alkenylaluminum dialkyl compound with an epoxide compound followed by hydrolysis. The alkenyl moiety has one or more double bond carbon-to-carbon linkage and from 5 to 20 carbon atoms that can be optionally substituted with the substituents selected from alkyl and aromatic radicals having 1 to 12 carbon atoms.
    Type: Grant
    Filed: March 11, 1976
    Date of Patent: January 9, 1979
    Assignee: Texas Alkyls, Inc.
    Inventors: Spencer C. Watson, Dennis B. Malpass, G. Scott Yeargin