The Bicyclo Lactone Consists Of Two Six-membered Rings And Is Unsubstituted Or Hydrocarbyl Substituted Only Patents (Class 549/290)
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Patent number: 6002020Abstract: 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: GrantFiled: January 27, 1999Date of Patent: December 14, 1999Assignee: Clariant GmbHInventors: Holger Geissler, Daniel Decker, Peter Gross
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Patent number: 5886211Abstract: 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: GrantFiled: March 18, 1998Date of Patent: March 23, 1999Assignees: Sagami Chemical Research Center, Iharanikkei Chemical Industry Co., LtdInventors: Kenji Hirai, Katsuyuki Masuda, Yoshihiro Takao, Masahide Sugiyama, Yukio Ono, Masahumi Matsuzawa
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Patent number: 5872265Abstract: 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: GrantFiled: March 17, 1997Date of Patent: February 16, 1999Assignee: Industrie Chimiche Caffaro S.P.A.Inventors: Stefano Alini, Livius Cotarca, Pietro Delogu
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Patent number: 5786490Abstract: 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: GrantFiled: April 10, 1997Date of Patent: July 28, 1998Assignee: The Lubrizol CorporationInventors: Jeffry G. Dietz, Mark R. Baker, Paul E. Adams
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Patent number: 5663370Abstract: 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: GrantFiled: August 8, 1996Date of Patent: September 2, 1997Assignee: Zeneca LimitedInventors: Martin Charles Bowden, Stephen Martin Brown
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Patent number: 5656656Abstract: 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: GrantFiled: May 23, 1995Date of Patent: August 12, 1997Assignee: Dompe Farmaceutici S.p.A.Inventors: Carmelo A. Gandolfi, Lorella Cotini, Marco Mantovanini, Gianfranco Caselli, Gaetano Clavenna, Claudio Omini
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Patent number: 5639893Abstract: 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: GrantFiled: July 17, 1996Date of Patent: June 17, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Iwamoto, Shin Tanaka
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Patent number: 5468854Abstract: 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: GrantFiled: July 22, 1993Date of Patent: November 21, 1995Assignee: Pharmaceutical Discovery CorporationInventors: R. Tyler McCabe, Brian R. de Costa
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Patent number: 5441974Abstract: 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: GrantFiled: May 25, 1994Date of Patent: August 15, 1995Assignee: G. D. Searle & Co.Inventors: Philippe R. Bovy, Thomas E. Rogers, Masateru Miyano, Joseph G. Rico
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Patent number: 5418254Abstract: 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: GrantFiled: May 4, 1994Date of Patent: May 23, 1995Assignee: G. D. Searle & Co.Inventors: Horng-Chih Huang, David R. Reitz
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Patent number: 5300662Abstract: 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: GrantFiled: October 26, 1992Date of Patent: April 5, 1994Assignee: Sumitomo Chemical Company, LimitedInventors: Yoshitaka Nishida, Kiyomi Sakai, Tamio Shirafuji
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Patent number: 5281721Abstract: 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: GrantFiled: April 28, 1992Date of Patent: January 25, 1994Assignee: Georgia Tech Research CorporationInventors: James C. Powers, Wade Harper
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Patent number: 5260457Abstract: 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: GrantFiled: July 30, 1992Date of Patent: November 9, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Yoshitaka Nishida, Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako
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Patent number: 5237075Abstract: 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: GrantFiled: February 24, 1992Date of Patent: August 17, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako, Itaru Kawata, Yasumoto Simazu, Tetuya Suzuta
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Patent number: 5231194Abstract: 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: GrantFiled: December 21, 1990Date of Patent: July 27, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako
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Patent number: 5218129Abstract: 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: GrantFiled: December 17, 1991Date of Patent: June 8, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Shirafuji, Kiyomi Sakai, Kensen Okusako, Yoshitaka Nishida
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Patent number: 5214160Abstract: 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: GrantFiled: September 25, 1992Date of Patent: May 25, 1993Assignee: Givaudan CorporationInventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
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Patent number: 5189043Abstract: 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: GrantFiled: October 26, 1990Date of Patent: February 23, 1993Assignee: Takeda Chemical Industries, Ltd.Inventors: Hideaki Natsugari, Hitoshi Ikeda
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Patent number: 5189180Abstract: 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: GrantFiled: May 1, 1991Date of Patent: February 23, 1993Assignee: E. R. Squibb & Sons, Inc.Inventor: Donald S. Karanewsky
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Patent number: 5180709Abstract: 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: GrantFiled: May 31, 1991Date of Patent: January 19, 1993Assignee: Givaudan-Roure CorporationInventors: Franz Etzweiler, Daniel Helmlinger, Cornelius Nussbaumer, Mario Pesaro
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Patent number: 5055582Abstract: 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: GrantFiled: December 13, 1988Date of Patent: October 8, 1991Assignee: National Research Development CorporationInventors: Robert B. Garland, Masateru Miyano
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Patent number: 4891298Abstract: 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: GrantFiled: October 3, 1988Date of Patent: January 2, 1990Assignee: Polaroid CorporationInventor: David P. Waller
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Patent number: 4886733Abstract: 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: GrantFiled: October 3, 1988Date of Patent: December 12, 1989Assignee: Polaroid CorporationInventor: Myron S. Simon
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Patent number: 4772728Abstract: 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: GrantFiled: August 19, 1985Date of Patent: September 20, 1988Assignee: Angus Chemical CompanyInventors: Stephan Korte, Craig W. Coulston, Friedhelm Korte
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Patent number: 4650881Abstract: 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: GrantFiled: April 1, 1985Date of Patent: March 17, 1987Assignee: Iowa State University Research Foundation, Inc.Inventors: Richard C. Larock, Sudarsanan Varaprath
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Patent number: 4647666Abstract: 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: GrantFiled: July 15, 1985Date of Patent: March 3, 1987Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4567281Abstract: 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: GrantFiled: June 6, 1983Date of Patent: January 28, 1986Assignee: The Dow Chemical CompanyInventor: Robert A. Dubois
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Patent number: 4417060Abstract: 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: GrantFiled: March 26, 1981Date of Patent: November 22, 1983Assignee: Jenoptik Jena GmbHInventors: Peter Czerney, Horst Hartmann, Jurgen Liebscher