The Bicyclo Lactone Consists Of Two Six-membered Rings And Is Unsubstituted Or Hydrocarbyl Substituted Only Patents (Class 549/290)
  • Patent number: 6002020
    Abstract: Good yields and selectivities are achieved in a process for preparing an isochroman-3-one of the formula (I) ##STR1## by reacting a 1,3-dihydroisobenzofuran of the formula (II) ##STR2## with carbon monoxide at a CO pressure of from 0.1 to 20 MPa in the presence of an ionic halide, a palladium catalyst and a dipolar aprotic solvent.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: December 14, 1999
    Assignee: Clariant GmbH
    Inventors: Holger Geissler, Daniel Decker, Peter Gross
  • Patent number: 5886211
    Abstract: 2-(Halomethyl)phenylacetic acid esters (3) which are useful as intermediates for producing agricultural fungicides are produced efficiently and conveniently by reacting a 3-isochromanone derivative (1) with a hydrogen halide and an alcohol or reacting (1) with a halomethyl alkyl ether and then reacting the product with an alcohol in the presence of a base. The starting compound, 3-isochromanone (1), is produced in good yield by reacting an .alpha.,.alpha.'-o-xylene dihalide (4) with carbon monoxide and water in an organic solvent in the presence of a palladium catalyst and an inorganic base and then treating the product with an acid.
    Type: Grant
    Filed: March 18, 1998
    Date of Patent: March 23, 1999
    Assignees: Sagami Chemical Research Center, Iharanikkei Chemical Industry Co., Ltd
    Inventors: Kenji Hirai, Katsuyuki Masuda, Yoshihiro Takao, Masahide Sugiyama, Yukio Ono, Masahumi Matsuzawa
  • Patent number: 5872265
    Abstract: A process for producing coumarin and substituted coumarins starting from substituted hexahydrocoumarins or from substituted dihydrocoumarins. The process includes dehydrogenation in the presence of catalysts based on metals of Group VIII of the periodic table of the elements and in the presence of at least one easily reducible organic compound. The invention allows to achieve exceptionally high yields that do not require the recycling of the hexahydrocoumarin or of the dihydrocoumarin that are present at the end of the reaction, and also allows to achieve high selectivity and easy purification.
    Type: Grant
    Filed: March 17, 1997
    Date of Patent: February 16, 1999
    Assignee: Industrie Chimiche Caffaro S.P.A.
    Inventors: Stefano Alini, Livius Cotarca, Pietro Delogu
  • Patent number: 5786490
    Abstract: A process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: July 28, 1998
    Assignee: The Lubrizol Corporation
    Inventors: Jeffry G. Dietz, Mark R. Baker, Paul E. Adams
  • Patent number: 5663370
    Abstract: Intermediates of formula (I), ##STR1## wherein R is H or CH.sub.3 ; processes for preparing them and their use as chemical intermediates, especially for preparing fungicidal acrylic ester derivatives.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: September 2, 1997
    Assignee: Zeneca Limited
    Inventors: Martin Charles Bowden, Stephen Martin Brown
  • Patent number: 5656656
    Abstract: Tartronic acid acetalic ethers and esters of the general formula: ##STR1## are provided and are useful in treatment of bone dysmetabolism. As examples, Ra and Rb may be hydrogen, B is a C.sub.2 -C.sub.12 acyl group, R is phenyl and n is 0-12.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: August 12, 1997
    Assignee: Dompe Farmaceutici S.p.A.
    Inventors: Carmelo A. Gandolfi, Lorella Cotini, Marco Mantovanini, Gianfranco Caselli, Gaetano Clavenna, Claudio Omini
  • Patent number: 5639893
    Abstract: The present invention involves the production of octahydrocoumarins from coumarins and/or 3,4-dihydrocoumarins in good yields by a simple process which can be industrially carried out, by reducing coumarins and/or 3,4-dihydrocoumarins to octohydrocoumarins with hydrogen in the presence of an alcohol and a ruthenium catalyst, and optionally heating resultant 3-(2-hydroxycyclohexyl) propionate contained in the reduction reaction mixture to conduct cyclization/dealcoholization and convert same to octohydrocoumarins.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: June 17, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Iwamoto, Shin Tanaka
  • Patent number: 5468854
    Abstract: Conjugates of fluorescent labels with specific, selective, and high affinity ligands for receptors have been synthesized and used to directly measure binding to receptors. In the examples, fluorescein conjugates of the high-affinity benzodiazepine receptor ligands Ro 15-1788 and Ro 7-1986 were synthesized. The binding of these fluorescent ligands (BD 621, BD 623 and BD 607) to benzodiazepine receptors was characterized by direct fluorescence measurement. Both the equilibrium dissociation constants (K.sub.D) of BD 621 and BD 607 and the maximum number of binding sites (B.sub.max) estimated by fluorescence monitoring were consistent with values obtained by using radioligand binding techniques. The binding of BD 621 and BD 607 assessed by fluorescence measurement was reversible, abolished by photoaffinity labeling with Ro 15-4513, and unaffected by a variety of substances that do not bind to benzodiazepine receptors.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: November 21, 1995
    Assignee: Pharmaceutical Discovery Corporation
    Inventors: R. Tyler McCabe, Brian R. de Costa
  • Patent number: 5441974
    Abstract: This invention relates to compounds having the following formula ##STR1## wherein Z is a lactone or a lactone which is fused to a benzene ring which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidines derivatives.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: August 15, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Philippe R. Bovy, Thomas E. Rogers, Masateru Miyano, Joseph G. Rico
  • Patent number: 5418254
    Abstract: A class of 2,3-substituted cyclopenta-2,4-dienyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula II: ##STR1## wherein each of R.sup.1 and R.sup.2 is independently selected from hydrido, lower alkyl, lower hydroxyalkyl, halo, lower haloalkyl, lower alkoxycarbonyl and carboxyl; and wherein each of R.sup.3 through R.sup.12 is independently selected from hydrido, halo, lower alkyl, lower alkylthio, cyano, hydroxyl, mercapto, lower haloalkyl, lower haloalkoxy, lower alkoxy, lower hydroxyalkyl, lower alkoxyalkyl, lower alkylsulfonyl, lower haloalkylsulfonyl and sulfamyl; provided R.sup.5 and R.sup.10 are not both hydrido or methoxy; or a pharmaceutically suitable salt or prodrug thereof.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: May 23, 1995
    Assignee: G. D. Searle & Co.
    Inventors: Horng-Chih Huang, David R. Reitz
  • Patent number: 5300662
    Abstract: A process for producing coumarin or a derivative thereof, which process comprises dehydrogenation of 3,4-dihydrocoumarin or a derivative thereof in the presence of a palladium catalyst by heating under reduced pressure.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: April 5, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshitaka Nishida, Kiyomi Sakai, Tamio Shirafuji
  • Patent number: 5281721
    Abstract: This invention relates to a novel class of heterocyclic compounds useful for selectively inhibiting elastase, selectively inhibiting chymotrypsin-like enzymes, selectively inhibiting trypsin-like enzymes, or for generally inhibiting serine proteases of all classes.
    Type: Grant
    Filed: April 28, 1992
    Date of Patent: January 25, 1994
    Assignee: Georgia Tech Research Corporation
    Inventors: James C. Powers, Wade Harper
  • Patent number: 5260457
    Abstract: A process for producing coumarin and a derivative thereof represented by formula (2): ##STR1## wherein R.sub.1 to R.sub.4 each represents a hydrogen atom, a methyl group, or an ethyl group, provided that at least two of R.sub.1 to R.sub.4 each represents a hydrogen atom,the process comprising the step of heating a 3-(2-cyclohexanoyl)propionic acid ester represented by formula (1): ##STR2## wherein R.sub.1 to R.sub.4 are as defined above and R.sub.5 represents an alkyl group having from 1 to 4 carbon atoms,in the presence of a palladium catalyst, thereby to allow the ester of formula (1) to undergo cyclization and dehydrogenation reactions, the latter stage of the reactions, in which the conversion of the 3-(2-cyclohexanoyl) propionic acid ester used as a starting material has reached about 80% or more, being conducted at a higher temperature than that for the former stage of the reactions.
    Type: Grant
    Filed: July 30, 1992
    Date of Patent: November 9, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Yoshitaka Nishida, Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako
  • Patent number: 5237075
    Abstract: A process for producing a 3,4-dihydrocoumarin compound represented by formula (II): ##STR1## wherein R.sub.1 to R.sub.4 are as defined in the specification, comprising the steps of:(1) heating a 3-(2-cyclohexanoyl)propionic acid ester compound represented by formula (I): ##STR2## wherein R.sub.1 R.sub.5 are as defined in the specification, in the presence of at least one solid metal catalyst, thereby to allow said compound of formula (I) to undergo ring formation and dehydrogenation to yield said 3,4-dihydrocoumarin compound of formula (II) and, as a by-product, a coumarin compound represented by formula (III): ##STR3## wherein R.sub.1 to R.sub.
    Type: Grant
    Filed: February 24, 1992
    Date of Patent: August 17, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako, Itaru Kawata, Yasumoto Simazu, Tetuya Suzuta
  • Patent number: 5231194
    Abstract: A process for producing a coumarin derivative represented by formula (II): ##STR1## wherein R.sub.1 to R.sub.4 are as defined in the specification, comprising the step of: subjecting to a ring formation and dehydrogenation reaction a 3-(2-cyclohexanoyl)-propionic acid ester derivative represented by formula (I): ##STR2## wherein R.sub.1 to R.sub.4 are as defined in the specification, the ring formation and dehydrogenation reaction being (1) conducted by use of a catalyst comprising a carrier having supported thereon palladium and either of chromium oxide and chromium hydroxide, or (2) conducted by use of a catalyst comprising a carrier having supported thereon palladium or a catalyst comprising a carrier having supported thereon palladium and either of chromium oxide and chromium hydroxide, in the presence of a promoter which is at least one member selected from the group consisting of magnesium trisilicate, zirconia, metallic chromium, and metallic tungsten.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: July 27, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako
  • Patent number: 5218129
    Abstract: A process for producing 3,4-dihydrocoumarin comprising cyclization and dehydrogenation of a 3-(2-cyclohexanoyl)propionic acid ester, in which a reaction mixture obtained by the cyclization and dehydrogenation is washed with an alkali to reduce the dihydrocinnamic acid content of the reaction mixture to 1% by weight or less and/or previously distilling the reaction mixture to remove high-boiling substances, and then subjected to rectification to recover 3,4-dihydrocoumarin. The thus obtained 3,4-dihydrocoumarin has high purity and high quality sufficient for use as a perfume as it is.
    Type: Grant
    Filed: December 17, 1991
    Date of Patent: June 8, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako, Yoshitaka Nishida
  • Patent number: 5214160
    Abstract: The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5,-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8 -octahydronapthalene.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: May 25, 1993
    Assignee: Givaudan Corporation
    Inventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
  • Patent number: 5189043
    Abstract: A compound of the formula (I): ##STR1## wherein X is --CH.sub.2 -CH.sub.2 -- or --CH.dbd.CH--,Y is ##STR2## Z is an oxygen or sulfur atom, R.sup.1 and R.sup.2 are independently a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group and ring A is an optionally substituted 6-membered homocyclic ring,or its ester or salt which is useful as an inhibitory agent for the biosynthesis of the cholesterol.
    Type: Grant
    Filed: October 26, 1990
    Date of Patent: February 23, 1993
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hideaki Natsugari, Hitoshi Ikeda
  • Patent number: 5189180
    Abstract: Seco-mevinic acid derivatives are provided which have the structure ##STR1## including all stereoisomers thereof, wherein Z is ##STR2## R is H, alkali metal or lower alkyl, R.sup.1 is H, lower alkyl, aryl, lower alkoxy, cycloalkyl, heteroaryl, aralkyl, heteroaralkyl or heterocyclic; R.sup.2 is lower alkyl, cycloalkyl or aralkyl, and X is O or NR.sup.5 wherein R.sup.5 is H or lower alkyl, and are HMG CoA reductase inhibitors and thus are useful as antihypercholesterolemic agents and in treating atherosclerosis.New intermediates for preparing the above seco-mevinic acid derivatives are also provided.
    Type: Grant
    Filed: May 1, 1991
    Date of Patent: February 23, 1993
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Donald S. Karanewsky
  • Patent number: 5180709
    Abstract: The invention concerns novel odorants of formula I wherein R is hydrogen or methyl. ##STR1## The invention also concerns fragrance compositions containing I. Formula I is intended to particularly embrace as the racemates, (.+-.)-3.alpha.-acetyl-3.beta.,4.beta.,5,5-tetramethyl-2,3,4,4a.beta.,5,6, 7,8-octahydronapthalene and (.+-.)-3.alpha.-acetyl-4.beta.,5,5-trimethyl-2,3.beta.,4,4a.beta.,5,6,7,8- octahydronapthalene.
    Type: Grant
    Filed: May 31, 1991
    Date of Patent: January 19, 1993
    Assignee: Givaudan-Roure Corporation
    Inventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
  • Patent number: 5055582
    Abstract: This invention relates to a process for preparing useful thromboxane A.sub.2 inhibiting (.+-.)7-[3.alpha.-[1-[[(phenylamino)thioxomethyl]hydrazono]ethyl]-1.alpha. ,4.alpha.-bicyclo[2.2.1]hept-2.beta.-yl]-heptenoic acids and useful derivatives thereof from (.+-.)octahydro-1.alpha.-methyl-3a.alpha.,7a.alpha.-4.alpha.,7.alpha.-meth ano-2H-inden-2-ones.
    Type: Grant
    Filed: December 13, 1988
    Date of Patent: October 8, 1991
    Assignee: National Research Development Corporation
    Inventors: Robert B. Garland, Masateru Miyano
  • Patent number: 4891298
    Abstract: This invention relates to diffusion transfer photographic processes adapted to be performed in the presence of ambient light and to diffusion transfer products useful in such processes wherein a substantial increase in opacification in the red and near infrared region of the visible spectrum and a substantial increase in opacification in the blue and green region is achieved by employing certain alkyl-substituted phenanthrol/carboxynaphthol phthaleins as the light-absorbing, pH-sensitive optical filter agent for the longer wavelength region of the visible spectrum.
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: January 2, 1990
    Assignee: Polaroid Corporation
    Inventor: David P. Waller
  • Patent number: 4886733
    Abstract: This invention relates to diffusion transfer photographic processes adapted to be performed in the presence of ambient light and to diffusion transfer products useful in such processes wherein unexpectedly enhanced opacification in the red and near infrared region of the visible spectrum is achieved by employing phenanthrol/carboxynaphthol phthaleins as the light-absorbing, pH-sensitive optical filter agent for the longer wavelength region of the visible spectrum.
    Type: Grant
    Filed: October 3, 1988
    Date of Patent: December 12, 1989
    Assignee: Polaroid Corporation
    Inventor: Myron S. Simon
  • Patent number: 4772728
    Abstract: A method for making a bicyclic lactone comprising heating under aqueous acidic conditions a beta, gamma unsaturated cyclic nitrile and an aldehyde, for a length of time sufficient to convert at least a portion of the reactants to a bicyclic lactone of the formula ##STR1## wherein R.sub.3 is --H; R.sub.4, R.sub.5, and R.sub.6 are independently selected from the group consisting of --H, --CH.sub.3 ; R.sub.2 is selected from the group consisting of --H, --CH.sub.3, and --CH.sub.3, and --C.sub.2 H.sub.5 ; R.sub.8 is --H or --CH.sub.3 ; m is an integer from 1 to 5; o is 0, 1, 2, or 3; and p is 0, 1, or 2; provided that the sum of m+o+p is an integer from 3 to 5; either R.sub.3 or R.sub.8 together with R.sub.7 represents a carbon-carbon bond. The method uses commercially available and relatively inexpensive raw materials as reactants.
    Type: Grant
    Filed: August 19, 1985
    Date of Patent: September 20, 1988
    Assignee: Angus Chemical Company
    Inventors: Stephan Korte, Craig W. Coulston, Friedhelm Korte
  • Patent number: 4650881
    Abstract: Arenes, such as benzoic acid and substituted benzoic acids, are readily thallated by thallium(III) compounds such as the trifluoroacetate and subsequently reacted with palladium chloride and simple olefins, dienes, allylic halides, vinyl halides, vinyl esters, or unsaturated cyclopropanes or unsaturated cyclobutanes to give isocoumarins.
    Type: Grant
    Filed: April 1, 1985
    Date of Patent: March 17, 1987
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Richard C. Larock, Sudarsanan Varaprath
  • Patent number: 4647666
    Abstract: Functionally substituted arenes selected from the group consisting of p-tolylacetic acid, N-methylbenzamide, benzamide and acetanilide which are thallated provide an organothallium salt which undergoes subsequent palladium promoted olefination to provide oxygen and/or nitrogen heterocycles such as ethers lactones, isoquinolones, indoles and isocarbostyrils.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: March 3, 1987
    Assignee: Iowa State University Research Foundation, Inc.
    Inventor: Richard C. Larock
  • Patent number: 4567281
    Abstract: This invention is a process for cyclizing an ortho-alkenyl arenol, wherein the double bond of the alkenyl moiety is one or two carbons removed from the aromatic ring, with carbon monoxide, wherein the process comprises contacting an ortho-alkenyl arenol with carbon monoxide in the presence of a catalytic amount of a catalyst comprising (1) a rhodium-carbonyl complex and (2) an amine with a pK.sub.a of 6 or greater, arsine, phosphine, stibine or mixture thereof, under conditions such that a lactone-fused aromatic compound is prepared.
    Type: Grant
    Filed: June 6, 1983
    Date of Patent: January 28, 1986
    Assignee: The Dow Chemical Company
    Inventor: Robert A. Dubois
  • Patent number: 4417060
    Abstract: The present invention is directed to novel amino-substituted 2-cumaryl-3'-chromenylium salts of the general formula ##STR1## wherein R.sup.3 and R.sup.7 are a dialkyl or cycloalkyl disubstituted amino group, hydrogen, or hydroxy group, provided that at least one of R.sup.3 and R.sup.7 is an amino group, R.sup.1, R.sup.2, R.sup.4, R.sup.5, R.sup.6, and R.sup.8 are hydrogen, an alkoxy group, or two of these substituents together form an aromatic ring, provided that R.sup.1, R.sup.2 and R.sup.4 may be the same or different, and R.sup.5, R.sup.6 and R.sup.8 may be the same or different, and Y.sup.- is an acidic anion and to the process for their preparation.
    Type: Grant
    Filed: March 26, 1981
    Date of Patent: November 22, 1983
    Assignee: Jenoptik Jena GmbH
    Inventors: Peter Czerney, Horst Hartmann, Jurgen Liebscher