The Lactone Ring Is Six-membered Patents (Class 549/273)
  • Publication number: 20010009964
    Abstract: The present invention relates to a catalyst for preparing a lactone, which is prepared by supporting a cupric compound, a zinc compound and at least one alkaline earth metal compound on the supporter. The present invention also relates to a method for preparing a lactone, which comprises a dehydrocyclization reaction of a diol under a gas phase in the presence of the aforementioned catalyst after activating said catalyst. The catalyst for preparing lactone of the present invention is quite economic because of its high activity, long lifetime and high selectivity of products.
    Type: Application
    Filed: December 15, 2000
    Publication date: July 26, 2001
    Applicant: DAIREN CHEMICAL CORPORATION
    Inventors: Shien-Chang Chen, Fu-Shen Lin, Liang-An Hsu, Cheng-Lin Tsai
  • Patent number: 6255276
    Abstract: The invention is concerned with odorant compositions which contain macrocycles, namely 15- to 17-membered compounds of the formula: wherein the dotted line signifies an optional additional bond, X and Y stand for methylene or C2-12-polymethylene, optionally substituted with an additional methyl group, and A signifies hydrogen or methyl in the case of the unsaturated compounds and methyl in the case of the saturated compounds, with the proviso that the unsaturated compounds are present to more than 80% in the cis form when A signifies hydrogen and are present to more than 50% in the cis form when A signifies methyl, with the exception of Z-oxacyclopentadec-6-en-2-one (15-membered ring), Z-oxacycloheptadec-8-en-2-one (17-membered ring), and Z-oxacycloheptadec-11-en-2-one (17-membered ring), a process for the manufacture of the compounds of formula I and the use of the compounds of formula I as odorants.
    Type: Grant
    Filed: February 16, 2000
    Date of Patent: July 3, 2001
    Assignee: Givauden Roure (International) S.A.
    Inventors: Georg Frater, Daniel Helmlinger, Urs Müller
  • Patent number: 6242616
    Abstract: Synthetic methods for lactone-containing compounds such as the discodermolides are provided, as are compounds which mimic the chemical and/or biological activity thereof, and methods and intermediates useful in their preparation.
    Type: Grant
    Filed: December 7, 1999
    Date of Patent: June 5, 2001
    Assignee: The Trustees of the University of Pennsylvania
    Inventors: Amos B. Smith, III, Thomas J. Beauchamp, Matthew J. LaMarche, Hirokazu Arimoto
  • Patent number: 6232474
    Abstract: This invention pertains to a process for making &agr;-methylenelactones and &agr;-substituted hydrocarbylidene lactones. The present invention obtains high yields of &agr;-methylene-&ggr;-butyrolactone by heating &ggr;-butyrolactone and formaldehyde in the presence of a base.
    Type: Grant
    Filed: March 27, 2000
    Date of Patent: May 15, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Charles Brandenburg, Randal King, Leo E. Manzer
  • Patent number: 6229023
    Abstract: According to the inventive co-oxidation process of organic compounds, (A) a compound selected from (A1) a compound having a non-aromatic ethylenic bond and (A2) a ketone or an alcohol corresponding to the ketone is oxidized by molecular oxygen in the presence of N-hydroxyphthalimide or another imide compound and in the coexistence of (B) a compound oxidizable by the imide compound and oxygen and different from the compound (A). As the compound (B), (a) primary or secondary alcohols (e.g., benzhydrol, cyclohexanol), (b) compounds each having a carbon-hydrogen bond at the adjacent position to an unsaturated bond (e.g., tetralin, ethylbenzene) and the like can be used. According to this process, a corresponding epoxy compound from the compound (A1) having a non-aromatic ethylenic bond, and a corresponding ester or lactone from the ketone or its corresponding alcohol (A2) can be obtained in satisfactory yields.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: May 8, 2001
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 6225476
    Abstract: Provided by the invention is a chemical-amplification positive-working photoresist composition used in the fine photolithographic patterning in the manufacturing process of semiconductor devices, which is suitable for the patterning light exposure with ArF excimer laser beams of very short wavelength by virtue of absence of aromatic structure in the ingredients of the composition. The composition comprises, as the film-forming resinous ingredient, an acrylic resin having unique monomeric units represented by the general formula &Brketopenst;CH2—CR1(—CO—O—CR2R3R4)&Brketclosest;, in which R1 is a hydrogen atom or a methyl group, R2 and R3 are each, independently from the other, an alkyl group having 1 to 4 carbon atoms and R4 is an alkoxycarbonyl group or a group derived from a molecule of a lactone compound or ketone compound by removing a hydrogen atom bonded to the carbon atom.
    Type: Grant
    Filed: April 4, 2000
    Date of Patent: May 1, 2001
    Assignee: Tokyo Ohka Kogyo Co., Ltd.
    Inventors: Hideo Hada, Kazufumi Sato, Hiroshi Komano
  • Patent number: 6214330
    Abstract: The present invention is directed to double prodrugs containing polymeric-based transport forms.
    Type: Grant
    Filed: July 13, 1998
    Date of Patent: April 10, 2001
    Assignee: Enzon, Inc.
    Inventors: Richard B. Greenwald, Yun H. Choc, Annapurna Pendri
  • Patent number: 6160173
    Abstract: The invention provides a process for the recovery of purified lactic acid values from an aqueous feed solution containing lactic acid, lactic acid salt, or mixtures thereof, comprising: bringing the feed solution into contact with a substantially immiscible anion exchanger to form a substantially water-immiscible phase comprising an anion exchanger-lactic acid adduct; effecting a condensation reaction in the substantially water-immiscible phase between a carboxylic moiety of the lactic acid adduct and a moiety selected from a hydroxyl moiety and a primary or secondary amine moiety to respectively form a lactic acid ester or amine product; and separating the formed lactic acid product from the anion exchanger.
    Type: Grant
    Filed: October 26, 1999
    Date of Patent: December 12, 2000
    Assignee: Cargill Incorporated
    Inventors: Aharon Meir Eyal, Patrick R. Gruber, Paul McWilliams, David R. Witzke
  • Patent number: 6130340
    Abstract: The present invention relates to a process for stereoselective cycloaddition reactions which generally comprises a cycloaddition reaction between a pair of chiral or prochiral substrates that contain reactive .pi.-systems, in the present of a non-racemic chiral catalyst, to produce a stereoisomerically enriched product.
    Type: Grant
    Filed: January 13, 1998
    Date of Patent: October 10, 2000
    Assignee: President and Fellows of Harvard College
    Inventors: Eric N. Jacobsen, Scott E. Schaus
  • Patent number: 6063938
    Abstract: Disclosed is a process for producing .epsilon.-caprolactone which comprises distilling a reaction mixture obtained by oxidation of cyclohexanone to separate impurities, wherein .epsilon.-caprolactone separated in a rectifying column is contacted with an oxygen-containing gas and then distilled. Thereby, a high quality of .epsilon.-caprolactone of in which no coloration occurs during long time preservation can be produced by industrial advantages.
    Type: Grant
    Filed: July 25, 1997
    Date of Patent: May 16, 2000
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuo Tanaka, Kengi Nakaya, Atsushi Ohkoshi, Hideaki Fujita
  • Patent number: 6060507
    Abstract: Massoialactone is useful for preventing or at least inhibiting growth of a fungus. Accordingly, a fungicidal composition has massoialactone as an active antifungal compound together with an agronomically acceptable carrier therefor. Additional antifungal ingredients can be added to the composition. The composition can be applied to surfaces, including surfaces of plants and plant parts, such as seeds.
    Type: Grant
    Filed: August 28, 1997
    Date of Patent: May 9, 2000
    Assignee: Horticulture and Food Research Institute of New Zealand Limited
    Inventors: Robert Anthony Hill, Horace G. Cutler, Stephen Robert Parker
  • Patent number: 6034255
    Abstract: The present invention provides novel haloenol lactones that are effective as active site inhibitors of cholesterol esterase. By inhibiting cholesterol esterase the inhibitors of the present invention provide a new approach to the treatment of hypercholesterolemia through limiting the bioavailability of dietary cholesterol.
    Type: Grant
    Filed: April 15, 1999
    Date of Patent: March 7, 2000
    Assignee: University of New Mexico
    Inventors: Lorraine Deck, David L. Vander Jagt
  • Patent number: 6022982
    Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids such as oleic acid is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.9 to .DELTA..sup.15 unsaturated fatty acids in the presence of an acid catalyst and at a temperature between about 20 to 70.degree. C. Moreover, yields of the .delta.-lactones may be increased even further by reaction in the presence of dipolar, non-participating, non-aqueous solvents. The unsaturated fatty acids may be free or esterified with glycerol or other aliphatic alcohols, and the .delta.-lactones may be produced by reacting mono-, di- or triglycerides of the unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the instant process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification or steam splitting.
    Type: Grant
    Filed: December 14, 1998
    Date of Patent: February 8, 2000
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Steven C. Cermak
  • Patent number: 6022887
    Abstract: Compounds of the formula ##STR1## wherein X in each of formulas (1) and (2) represents a substituted or unsubstituted alkylene, alkenylene, or alkynylene linker of 2-6C;Y represents one or more carbocyclic or heterocyclic rings; when two or more rings are present in Y, they may optionally be fused; andR' represents a cation, H or a substituted or unsubstituted alkyl group of 1-6C; andthe dotted lines represent optional .pi.-bonds,promote bone formation and are thus usefull in treating osteoporosis, bone fracture or deficiency, primary or secondary hyperparathyroidism, periodontal disease or defect, metastatic bone disease, osteolytic bone disease, post-plastic surgery, post-prosthetic joint surgery, and post-dental implantation.
    Type: Grant
    Filed: December 12, 1997
    Date of Patent: February 8, 2000
    Assignees: OsteoScreen, Inc., ZymoGenetics Corporation
    Inventors: Shirley R. Gasper, Robert R. West, Theresa Martinez, Kirk G. Robbins, Patricia A. McKernan, Nand Baindur, Virender M. Labroo
  • Patent number: 6005103
    Abstract: The present invention relates to novel tri- and tetrasubstituted pyrones and related structures which potently inhibit the HIV aspartyl protease blocking HIV infectivity. The pyrone derivatives are useful in the development of therapies for the treatment of bacterial and viral infections and diseases, including AIDS. The present invention is also directed to methods of synthesis of multifunctionalized pyrones and of related structures.
    Type: Grant
    Filed: October 12, 1994
    Date of Patent: December 21, 1999
    Assignee: Warner-Lambert Company
    Inventors: John Michael Domagala, Elizabeth Lunney, Kimberly Suzanne Para, Josyula Venkata Nagendra Vara Prasad, Bradley Dean Tait
  • Patent number: 5883266
    Abstract: The present invention is based upon the surprising discovery that a 5-carbon compound selected from the group of 4-oxopentanoic acid, at least one lactone of 4-oxopentanoic acid, and combinations thereof, may be hydrogenated with a bimetallic catalyst of a noble metal in combination with a second metal and preserve the pendant methyl group. It was further unexpectedly discovered that the same conditions of bimetallic catalyst in the presence of hydrogen are useful for catalyzing the different intermediate reactions for example angelicalactone to gamma-valerolactone and gamma-valerolactone to 1,4-pentanediol. Finally, it was surprising that levulinic acid could be converted to 2-methyltetrahydrofuran with heating in the presence of the bimetallic catalyst and hydrogen in a single process vessel. The method of the present invention unexpectedly produced a fuel or fuel component having 2-methyltetrahydrofuran either in a yield greater than 4.5 mol % or in combination with alcohols.
    Type: Grant
    Filed: January 16, 1998
    Date of Patent: March 16, 1999
    Assignee: Battelle Memorial Institute
    Inventors: Douglas C. Elliott, John G. Frye
  • Patent number: 5849935
    Abstract: An improved process for the production of high yields of .delta.-lactones and 5-hydroxy fatty acids from unsaturated fatty acids which are free or esterified with glycerol is disclosed. The .delta.-lactones may be produced by reacting one or more .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids in the presence of an acid, clay or zeolite catalyst. Alternatively, the .delta.-lactones may be produced by reacting one or more triglycerides which are esters of glycerol with .DELTA..sup.5 or .DELTA..sup.6 unsaturated fatty acids with the same catalysts. Because the .delta.-lactones may be produced from the triglycerides of unsaturated fatty acids, the process may be practiced using naturally occurring plant oils directly, without the need for any preliminary steps of saponification. Optionally, the .delta.-lactones so formed may be further reacted with an alkali in an aqueous solution to produce 5-hydroxy fatty acids.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: December 15, 1998
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Terry A. Isbell, Beth A. Plattner, Robert Kleiman
  • Patent number: 5840920
    Abstract: A process for reacting olefinic compounds, certain carboxylic reactants, and aldehydes or ketones and products prepared by the process. The compositions of the process are useful as intermediates for the preparation of additives for lubricants and fuels.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: November 24, 1998
    Assignee: The Lubrizol Corporation
    Inventor: Mark R. Baker
  • Patent number: 5767147
    Abstract: This invention relates to novel haloenol lactone compounds. These compounds have the following general structure: ##STR1## in which Ar is an aryl group and Y is a haloenol lactone moiety. The compounds of the invention are useful for the specific measurement of particular isoenzymes of glutathione S-transferase. Measurement of glutathione S-transferase isoenzymes has importance in diagnostic medicine. The compounds of the invention are also useful for treatment of drug resistance in cancer and for preventing herbicide resistance in plants.
    Type: Grant
    Filed: April 21, 1995
    Date of Patent: June 16, 1998
    Assignee: The Regents of the University of California
    Inventors: A. Daniel Jones, Alyson E. Mitchell, Bruce D. Hammock, Jiang Zheng
  • Patent number: 5731293
    Abstract: A compound of the formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are, independently, --CON(R.sup.4)R.sup.5, or a monosaccharide, or acylated monosaccharide group, with the proviso that at least one of R.sup.1 and R.sup.2 is --CON(R.sup.4)R.sup.5, and R.sup.4 and R.sup.5 are, independently, a hydrogen atom, or a hydroxyl, alkyl, aryl, or aralkyl group, or R.sup.4 and R.sup.5 together with the nitrogen atom attached thereto form a 3- to 7-membered saturated cycloaliphatic amino group, and R.sup.3 is a hydrogen atom, or a hydroxyl, alkyl, aryl, aralkyl, or --COOR.sup.8 group, and R.sup.3 is at 3- or 4-position, and R.sup.8 is a hydrogen atom or an alkyl group, or a salt thereof is disclosed. The compound has a function to inhibit a matrix metalloproteinase.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: March 24, 1998
    Assignee: Kureha Chemical Industry Co., Ltd.
    Inventors: Koju Watanabe, Koichi Niimura, Toru Yamazaki, Hiroshi Maruoka
  • Patent number: 5714618
    Abstract: A polymer having a blocked terminal group according to the present invention, represented by the following Formula (I): ##STR1## where R is an alkylene group containing 1 to 20 carbon atoms; X.sub.1 is an acyl group containing 2 to 50 carbon atoms; Y is H, an alkyl group containing 1 to 50 carbon atoms or an alkenyl group containing 1 to 50 carbon atoms; m is a positive integer; and n.sub.1 is 0 or a positive integer.
    Type: Grant
    Filed: January 9, 1997
    Date of Patent: February 3, 1998
    Assignee: Toyo Boseki Kabushiki Kaisha
    Inventors: Kunio Kimura, Takeshi Ito, Tomohiro Aoyama, Keiichi Uno, Kiyoshi Hotta, Minako Arichi
  • Patent number: 5684152
    Abstract: Carboxy-peptidyl compounds of Formula I are found to be useful inhibitors of matrix metalloendoproteinase-mediated diseases including osteoarthritis, rheumatoid arthritis, septic arthritis, tumor invasion in certain cancers, periodontal disease, corneal ulceration, proteinuria, dystrophobic epidermolysis bullosa, coronary thrombosis associated with atherosclerotic plaque rupture, and aneurysmal aortic disease. This invention relates to a process of making the carboxy-peptidyl compounds of formula I.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: November 4, 1997
    Assignee: Merck & Co., Inc.
    Inventors: Mitree M. Ponpipom, William K. Hagmann
  • Patent number: 5677263
    Abstract: 5-Tetrahydropyranone cyclohexenone oxime ethers I ##STR1## where R.sup.1 =C.sub.1 -C.sub.6 -alkylR.sup.2 =phenyl which can have attached to it 1-3 substituents; C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.4 -alkenyl or C.sub.3 -C.sub.4 -alkynyl, each of which can be substituted by halogen, C.sub.1 -C.sub.3 -alkyl, unsubstituted or substituted phenyl or unsubstituted or substituted phenoxy;and their agriculturally useful salts and esters.
    Type: Grant
    Filed: February 15, 1996
    Date of Patent: October 14, 1997
    Assignee: Basf Aktiengesellschaft
    Inventors: Joachim Rheinheimer, Ulf Misslitz, Uwe Kardorff, Karl-Otto Westphalen, Helmut Walter
  • Patent number: 5670661
    Abstract: The present invention relates to a process for producing lactones starting from cyclic ketones which comprises an oxidation reaction which is performed in the presence of an optionally substituted cycloaliphatic peracid or of an optionally substituted aliphatic peracid that is immiscible with water. The process allows to obtain high selectivity, does not entail the use of dangerous reagents, and allows excellent economic advantages.
    Type: Grant
    Filed: April 16, 1996
    Date of Patent: September 23, 1997
    Assignee: Industrie Chimiche Caffaro S.p.A.
    Inventors: Livius Cotarca, Roberto Bianchini
  • Patent number: 5665891
    Abstract: A process for the catalysed oxidation of ketones to esters or lactones with hydrogen peroxide in the presence of a carboxylic acid or anhydride is provided. The process employs gamma alumina as a heterogeneous catalyst. In certain preferred embodiments the catalyst also contains a tungsten-containing heteropolyacid. Preferably, the heteropolyacid contains phosphorus. In a related process, the catalyst accelerates the formation of percarboxylic acid solutions.
    Type: Grant
    Filed: October 12, 1995
    Date of Patent: September 9, 1997
    Assignee: Solvay Interox Limited
    Inventors: Scott William Brown, Alexander Johnstone, William Ronald Sanderson
  • Patent number: 5631365
    Abstract: A process for preparing compounds of the formula ##STR1## wherein R and R.sup.2 are independently --OH, --O(lower alkyl) or --0-benzyl and the remaining variables are as defined in the specification, comprising(a) treating with a strong base in an anhydrous organic solvent a lactone of the formula ##STR2## respectively, wherein Ar.sup.10 is Ar.sup.1 or a suitably protected hydroxy- or amino-substituted aryl, and R' and R.sup.2' are R and R.sup.2 as defined above or are suitably protected hydroxy groups;(b) reacting a product of step (a) with an imine of the formula ##STR3## wherein Ar.sup.20 and Ar.sup.30 are Ar.sup.2 or Ar.sup.3 or suitably protected hydroxy- or amino-substituted aryl;c) quenching the reaction with an acid; andd) removing protecting groups as necssary.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: May 20, 1997
    Assignee: Schering Corporation
    Inventors: Stuart B. Rosenblum, Sundeep Dugar, Duane A. Burnett, John W. Clader, Brian A. McKittrick
  • Patent number: 5622821
    Abstract: The invention provides lanthanide chelates capable of intense luminescence. The celates comprise a lanthanide chelator covalently joined to a coumarin-like or quinolone-like sensitizer. Exemplary sensitzers include 2- or 4-quinolones, 2- or 4-coumarins, or derivatives thereof e.g. carbostyril 124 (7-amino-4-methyl-2-quinolone), coumarin 120 (7-amino-4-methyl-2-coumarin), coumarin 124 (7-amino-4-(trifluoromethyl)-2-coumarin), aminomethyltrimethylpsoralen, etc.The chelates form high affinity complexes with lanthanides, such as terbium or europium, through chelator groups, such as DTPA. The chelates may be coupled to a wide variety of compounds to create specific labels, probes, diagnostic and/or therapeutic reagents, etc. The chelates find particular use in resonance energy transfer between chelate-lanthanide complexes and another luminescent agent, often a fluorescent non-metal based resonance energy acceptor.
    Type: Grant
    Filed: June 29, 1994
    Date of Patent: April 22, 1997
    Assignee: The Regents of the University of California
    Inventors: Paul R. Selvin, John Hearst
  • Patent number: 5504106
    Abstract: This invention relates to phenyl amidine alkanoic acids and lactones having the following formula ##STR1## or a pharmaceutically acceptable salt which are useful in the inhibition of platelet aggregation. This invention also relates to pharmaceutical compositions of such phenyl amidine derivatives.
    Type: Grant
    Filed: July 21, 1994
    Date of Patent: April 2, 1996
    Assignee: G. D. Searle & Co.
    Inventors: Norman A. Abood, Robert E. Manning, Masateru Miyano
  • Patent number: 5498734
    Abstract: The magnesium complexes of cyclic hydrocarbons containing conjugated dienes, such as 1,2-dimethylenecycloalkanes, and 1,3-butadienes, are readily prepared in high yields using highly reactive magnesium. Reactions of these (2-butene-1,4 diyl)magnesium reagents with electrophiles such as dibromoalkanes, alkylditosylates, alkylditriflates, bromoalkylnitriles, esters, or amides serve as a convenient method for synthesizing carbocyclic systems. Significantly, carbocycles prepared by this method contain functional groups such as the exocyclic double bond or a keto group in one of the rings which could be used for further elaboration of these molecules. Furthermore, fused bicyclic systems containing a substituted five-membered ring can be conveniently prepared at high temperatures by the reactions of (2-butene-1,4-diyl)magnesium complexes with carboxylic esters or acid halides whereas low temperatures lead to regioselective synthesis of .beta.,.gamma.-unsaturated ketones. Additionally, .gamma.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: March 12, 1996
    Assignee: University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5480580
    Abstract: Optical active compounds which are chemically stable, are not colored, have a good optical stability, and which give a liquid crystal composition having a large spontaneous polarization when the compound is incorporated, are provided. The optical active compound have an asymmetric carbon atom fixed by a .delta.-valerolactone ring and the permanent dipole moment derived from the carboxylic group is fixed by the .delta.-valerolactone ring and two alkyl groups which can be regarded as a part of a measogen.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: January 2, 1996
    Assignee: Mitsubishi Rayon Company Ltd.
    Inventors: Keiichi Sakashita, Yoshitaka Kageyama, Tetsuya Ikemoto
  • Patent number: 5463085
    Abstract: A synthesis method of physiologically active .delta.-lactone, which comprises addition-reacting diethyl methylmalonate and methacrolein in the presence of a base.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: October 31, 1995
    Assignee: Nitto Denko Corporation
    Inventors: Tetsuo Omata, Kaichi Tanida
  • Patent number: 5416224
    Abstract: A convenient stereoselective process for the preparation of .alpha.-alkylidene-substituted-.gamma.-butyrolactones and .delta.-valerolactones is provided. The process involves reacting an .alpha.-acyl lactone, an aldehyde, and an alkali metal hydroxide in an inert diluent at an elevated temperature while removing water.
    Type: Grant
    Filed: December 12, 1990
    Date of Patent: May 16, 1995
    Assignee: Henkel Corporation
    Inventor: Louis Rebrovic
  • Patent number: 5414016
    Abstract: Leukotriene-B.sub.4 derivatives of formula I ##STR1## are described, in which R.sup.1 means CH.sub.2 OH, CH.sub.3, CF.sub.3, COOR.sup.5, CONR.sup.6 R.sup.7, orR.sup.1 together with R.sup.2 means a carbonyl group,R.sup.4 symbolizes H, C.sub.1 -C.sub.10 alkyl optionally substituted, C.sub.3 -C.sub.10 cycloalkyl, C.sub.6 -C.sub.10 aryl radical optionally substituted, or a 5-6-membered aromatic heterocyclic ring,A symbolizes a trans, trans-CH.dbd.CH--CH.dbd.CH, a --CH.sub.2 CH.sub.2 --CH.dbd.CH-- or a tetramethylene group,B symbolizes a C.sub.1 -C.sub.10 alkylene group, which optionally can be substituted by fluorine or the group ##STR2## D can mean a direct bond, oxygen, sulfur, --C.tbd.C--, --CH.dbd.CR.sup.6 or together withB can also mean a direct bond, their salts with physiologically compatible bases and their cyclodextrin clathrates.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: May 9, 1995
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt, Claudia Giesen
  • Patent number: 5405974
    Abstract: A process for producing a lactone or an ester represented by the following general formula (2), wherein R.sup.1 and R.sup.2, identical or different, each represents (C.sub.1 --C.sub.20) alkyl group; alkyl group substituted with a terminal alkenyl, halogen, alkoxy, phenoxy or acyloxy; phenyl group; or phenyl group substituted with alkyl, halogen, alkoxy, phenoxy or acyloxy; phenylalkyl group; or phenylalkyl group substituted with alkyl, halogen, alkoxy, phenoxy or acyloxy; provided that when R.sup.1 and R.sup.2, identical or different, each represents unsubstituted alkyl group or alkyl group substituted with a terminal alkenyl, halogen, alkoxy, phenoxy, acyloxy or phenyl, the respective alkyl parts of R.sup.1 and R.sup.2 may be conjunct to each other; which comprises reacting a ketone represented by the following general formula (1), wherein R.sup.1 and R.sup.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: April 11, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • Patent number: 5384078
    Abstract: A soluble highly reactive form of calcium, prepared from Ca(II) salts and a reducing agent in ethereal, polyethereal, or hydrocarbon solvents, is presented. This form of calcium can be used in the preparation of organocalcium reagents. The organocalcium reagents resulting from the reaction of the soluble highly reactive calcium with organic compounds containing either halide, cyanide, a 1,3-diene, or a polyunsaturated functionality, are stable, useful reagents for organic synthesis. The organocalcium halide reagents undergo Grignard-type reactions. They also undergo reactions with Cu(I) salts to form organocalcium cuprate reagents. The organocalcium cuprate reagents undergo a variety of cross-coupling reactions. The soluble highly reactive calcium reacts with 1,3-dienes to yield the corresponding 2-butene-1,4-diylcalcium complexes. These bis-organocalcium reagents can undergo dialkylation reactions with .alpha.,.omega.
    Type: Grant
    Filed: December 15, 1993
    Date of Patent: January 24, 1995
    Assignee: Board of Regents of the University of Nebraska
    Inventor: Reuben D. Rieke
  • Patent number: 5338482
    Abstract: Liquid crystalline compounds having an optically active .gamma.-lactone ring of the general formula (A): ##STR1## wherein R.sup.1 is a group selected from the class consisting of ##STR2## n and e are each independently 0 or 1, R.sup.3 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, said alkyl and alkenyl groups having each optionally one or more asymmetric carbon atoms, X and Y are each hydrogen atom, a halogen atom or a cyano group, R.sup.2 is an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, said alkyl and alkenyl groups having each optionally one or more asymmetric carbon atoms, and * means an asymmetric carbon atom, a liquid crystal composition Containing the same and an element for opto-electronics devices comprising the liquid crystal composition.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: August 16, 1994
    Assignee: Daiso Co., Ltd.
    Inventors: Kazuhiko Sakaguchi, Tohru Kitamura
  • Patent number: 5310944
    Abstract: A process for producing a carboxylated compound, which comprises reacting a carbonyl compound with hydrogen peroxide in the presence of an organo-arsenic acid of the formula (1), ##STR1## wherein: R.sup.1 is a C.sub.1 -C.sub.12 alkyl group which may be substituted or an aryl group which may be substituted,R.sup.2 is a hydroxyl group or the same group as that which defines R.sup.1,or alternatively, R.sup.1 and R.sup.2 may bond to each other to form a five-membered or six-membered ring together with As atoms to which these groups are bonded, andthe substituent(s) substituted on the above groups is/are selected from hydroxyl, carboxyl, carbonyl, sulfonyl, sulfonium, an amino group, an ammonium group, an alkyl group, an alkoxyl group and a halogen atom,while a water concentration in a reaction system is maintained at not more than 2% by weight, thereby to form a corresponding carboxylated compound.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: May 10, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takao Kawaki, Yuh Miyauchi, Toshio Watanabe, Katsushige Hayashi, Satoshi Ueno, Hiroshi Ogawa, Fumiya Zaima
  • Patent number: 5292891
    Abstract: There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: March 8, 1994
    Assignee: Chisso Corporation
    Inventors: Chikara Kaneko, Masayuki Sato
  • Patent number: 5292907
    Abstract: The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.The invention also relates to intermediates obtained in the said manufacturing process.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: March 8, 1994
    Assignee: L'Oreal
    Inventors: Jean Maignan, Guy Solladie, Guy Stone
  • Patent number: 5278321
    Abstract: A process for simultaneously producing a lactone and an aromatic carboxylic acid, which comprises oxidizing a cyclic ketone and an aromatic aldehyde wherein: the cyclic ketone/aromatic aldehyde molar ratio is set at 1.1:1 to 20:1 and the throughput of the aromatic aldehyde per a unit reaction solution volume and a unit time is set at 0.05 to 1.5 mol/1.hour.
    Type: Grant
    Filed: August 11, 1992
    Date of Patent: January 11, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toru Tanaka, Kazuo Tanaka
  • Patent number: 5268507
    Abstract: Depolymerizing high molecular weight polyhydroxy acid by reacting with an amine to produce an amide derivative.
    Type: Grant
    Filed: November 22, 1991
    Date of Patent: December 7, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Loren D. Brake
  • Patent number: 5256800
    Abstract: There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Furthermore, a method for preparing an optically active compound comprises reacting a racemic 1,3-dioxin-4-one with vinylacetate in the presence of lipase to resolve the racemic compound into optically active compound represented by the formula (3) ##STR1## and an optically active compound represented by the formula (4) ##STR2## which is an antipode of the compound represented by the formula (3).
    Type: Grant
    Filed: February 18, 1992
    Date of Patent: October 26, 1993
    Assignee: Chisso Corporation
    Inventors: Chikara Kaneko, Masayuki Sato
  • Patent number: 5248792
    Abstract: The invention concerns odorant and flavorant compositions which contain one or more compounds of the formula ##STR1## wherein R represents an alkyl group having from three to eight carbon atoms. The invention also concerns 5-methyl-6-pentyl-tetrahydro-.alpha.-pyrone (compound of formula I in which R represents pentyl) in the form of its cis-isomer, its trans-isomer or its cis/trans isomer mixture, and a process for its manufacture by a Bayer-Villiger oxidation of 2-pentyl-3-methyl-cyclopentan-1-one. As fields of use for these compounds there come into consideration, for example, perfume and flavoring compositions, foodstuffs, semi-luxury consumables and drinks.
    Type: Grant
    Filed: May 13, 1992
    Date of Patent: September 28, 1993
    Assignee: Givaudan-Roure Corporation
    Inventor: Roman Kaiser
  • Patent number: 5231192
    Abstract: Process for the preparation of .alpha.-alkyl lactones by the steps of first reacting an .alpha.-acyl lactone, an aldehyde, and an alkali metal hydroxide together to form an .alpha.-alkylidene lactone, and then hydrogenating the .alpha.-alkylidene lactone.
    Type: Grant
    Filed: November 29, 1990
    Date of Patent: July 27, 1993
    Assignee: Henkel Corporation
    Inventors: Louis Rebrovic, Eugene G. Harris
  • Patent number: 5227399
    Abstract: Compounds having the formula I: ##STR1## are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating angina, cerebral spasm, glomerular nephritis, hepatitis, endotoxemia, uveitis and allograft rejection and in preventing the formation of atherosclerotic plaques.
    Type: Grant
    Filed: October 26, 1992
    Date of Patent: July 13, 1993
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Yves Girard, John W. Gillard, Laird A. Trimble, John Scheigetz, James A. Yergey, Yves Ducharme, Deborah A. Nicoll-Griffith, John H. Hutchinson
  • Patent number: 5210227
    Abstract: Compounds of formula I, ##STR1## wherein R.sup.1 represents H, OH, protected OH or alkoxy; R.sup.2 represents H; R.sup.3 represents O or (H,OH); R.sup.4 represents methyl, ethyl, propyl or allyl; R.sup.5 represents OH, protected OH or alkoxy; R.sup.6 represents OH; R.sup.7 represents OH, alkoxy or NR.sup.8 R.sup.9 where R.sup.8 and R.sup.9 independently represent H, alkyl or aryl; in addition, R.sup.1 and R.sup.2 may together represent a second bond between the carbon atoms to which they are attached; and R.sup.6 and R.sup.7 may together represent O; and pharmaceutically acceptable salts thereof; are useful inter alia as immunosuppressive agents. The invention also provides the novel compounds of formula I.
    Type: Grant
    Filed: February 27, 1991
    Date of Patent: May 11, 1993
    Assignees: Fisons plc, Fujisawa Pharmaceutical Company Limited
    Inventors: Hirokazu Tanaka, Martin E. Cooper, David K. Donald
  • Patent number: 5175310
    Abstract: A process is provided for producing alkylthio-substituted carboxylic acids and arylthio-substituted carboxylic acids and their corresponding alkylthio-substituted thioesters and arylthio-substituted thioesters. The process comprises reacting a mercaptan with a lactone in the presence of an acidic catalyst at temperatures of about 100.degree. C. to about 350.degree. C. The process for preparing the thio-substituted carboxylic acids and thio-substituted thioesters may be a continuous process or a batch process.
    Type: Grant
    Filed: March 16, 1990
    Date of Patent: December 29, 1992
    Assignee: Elf Atochem North America, Inc.
    Inventors: Michael J. Lindstrom, Bernard Buchholz, Robert B. Hager
  • Patent number: 5166366
    Abstract: Described is a process for the preparation of compositions of matter containing octalactones defined according to the structure: ##STR1## which includes the stereoisomers having the structures: ##STR2## by means of the sequential steps of (i) fermentation of caprylic acid or the ethyl ester of caprylic acid defined according to the generic structure: ##STR3## wherein R is hydrogen or ethyl using a microorganism selected from the group consisting of:Mortierella isabellina, ATCC 44583;Mortierella isabellina, ATCC 38063;Syncephalastrum racemosum, NRRL A-5889;Mortierella isabellina, IFO 7884;Mortierella ramanniana var. angulispora, IFO 8187;Mortierella isabellina, CBS 221.
    Type: Grant
    Filed: January 23, 1992
    Date of Patent: November 24, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Lynda B. McLean, James A. Morris, Henry A. Bondarovich
  • Patent number: 5149462
    Abstract: Disclosed is an optically active compound represented by the formula: ##STR1## wherein R.sub.1 and R.sub.2 are alkyl, alkenyl or alkoxy-alkyl, which may be substituted by halogen, X and U are a direct bond, --O--, --COO-- or --OCO--, Y and Z are a direct bond, --COO--, --OCO--, --CH.sub.2 O-- or --OCH.sub.2 --, A.sub.1 and A.sub.2 are phenylene, cyclohexylene or a phenylene- or cyclohexylene-containing group, p and q are 0 or 1, C* is an asymmetric carbon atom, with the proviso that when Z is a direct bond, q is 0, R.sub.2 is alkyl, Y is a direct bond, --OCO-- or --OCH.sub.2 --. The optically active compound is used as a ferroelectric liquid crystal or an additive to a ferroelectric or non-ferroelectric liquid crystal.
    Type: Grant
    Filed: July 12, 1990
    Date of Patent: September 22, 1992
    Assignee: Mitsubishi Rayon Company Ltd.
    Inventors: Keiichi Sakashita, Seiji Hayashi, Tetsuya Ikemoto, Osamu Yamamoto
  • Patent number: 5136055
    Abstract: A 21-carbon aliphatic branched chain dicarboxylic acid and a 21-carbon lactone are produced by reacting fatty acid (which contains linoleic acid) with acrylic acid via iodine catalysis, and subsequently removing from the low monomer reaction product the resulting C-21 lactone via solvent extraction with acetonitrile and hexane or heptane. The reaction products are distilled to yield dicarboxylic acid and lactone of high purity.
    Type: Grant
    Filed: September 3, 1991
    Date of Patent: August 4, 1992
    Assignee: Westvaco Corporation
    Inventor: Yvette A. Tramount