The Lactone Ring Has At Least Seven Members Patents (Class 549/266)
  • 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: 5534537
    Abstract: The present invention comprises peptidomimetic compounds which comprise a suitably substituted aminoalkylbenzamide moiety. The instant compounds inhibit the farnesyl protein transferase enzyme and the farnesylation of certain proteins. Furthermore, the instant farnesyl protein transferase inhibitors differ from those previously described as inhibitors of farnesyl-protein transferase in that they do not have a thiol moiety. The lack of the thiol offers unique advantages in terms of improved pharmacokinetic behavior in animals, prevention of thiol-dependent chemical reactions, such as rapid autoxidation and disulfide formation with endogenous thiols, and reduced systemic toxicity. Further contained in this invention are chemotherapeutic compositions containing these farnesyl transferase inhibitors and methods for their production.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: July 9, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Terrence M. Ciccarone, Suzanne C. MacTough, Theresa M. Williams
  • Patent number: 5474705
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) an aliphatic fluorocarbon terminal portion containing at least two catenary ether oxygen atoms; (b) a chiral, aliphatic hydrocarbon terminal portion; and (c) a central core connecting the terminal portions. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: November 14, 1994
    Date of Patent: December 12, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Eugene P. Janulis, Gilbert C. Johnson, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 5426195
    Abstract: Diols of 3 to 10 carbon atoms are catalytically dehydrogenated over a catalyst containing copper and chromium in a first stage in which the diols are passed in the liquid phase over the catalyst, and subsequently the reaction product obtained is passed in the gas phase over the catalyst.
    Type: Grant
    Filed: May 17, 1994
    Date of Patent: June 20, 1995
    Assignee: Huels Aktiengesellschaft
    Inventors: Reinhard Sigg, Hans Regner
  • 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: 5399718
    Abstract: A liquid phase process for making perfluorinated organic substances which comprises directly contacting in a temperature-controlled reactor a diluted solution or dispersion of a perfluorinateable, organic substance in a liquid, inert medium with a stoichiometric excess of fluorine gas, optionally diluted with an inert gas, to perfluorinate said organic substance at a temperature and a flow rate of inert gas (if used) sufficient to volatilize the resulting by-product hydrogen fluoride, removing said hydrogen fluoride from the reactor as it is produced, and separately removing from the reactor the resultant solution or dispersion of perfluorinated organic substance.
    Type: Grant
    Filed: February 1, 1994
    Date of Patent: March 21, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Michael G. Costello, George G. I. Moore
  • 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: 5260426
    Abstract: The invention relates to antibacterial pseudo-primycin complexes of formula (I) ##STR1## to the components and acid addition salts thereof, as well as to the preparation of these compounds and to the pharmaceutical compositions containing said compounds as active ingredient.In the formula (I) R.sup.1 is butyl, pentyl or hexyl, R.sup.2 is hydrogen, hydroxyl or O-arabinose and X is organic or inorganic acid ion.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: November 9, 1993
    Assignee: Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.
    Inventors: Gyula Dekany, Judit Frank, Istvan Pelczer, Gabor Kulcsar, Eniko Schreiner
  • Patent number: 5250707
    Abstract: Disclosed is a process for preparing .epsilon.-caprolactone comprising using a percarboxylic acid solution obtained by oxidizing organic carboxylic acid in an organic solvent in the presence of hydrogen peroxide and a boric acid catalyst, and cyclohexanone, supplying 1 to 1.5 mole of percarboxylic acid, 0.012 mole or less of hydrogen peroxide and 0.04 mole or less of the boric acid catalyst per mole of cyclohexanone in a reaction system, and reacting said cyclohexanone with said percarboxylic acid to form .epsilon.-caprolactone.
    Type: Grant
    Filed: April 22, 1991
    Date of Patent: October 5, 1993
    Assignee: Ube Industries, Ltd.
    Inventors: Yukio Inaba, Yohsuke Ueno, Takafumi Hirakawa, Suzuo Takiguchi
  • Patent number: 5217990
    Abstract: The use is described of macrolactones, such as cladospolides and patulolides, as medicaments for the treatment of allergic-inflammatory diseases.
    Type: Grant
    Filed: August 19, 1991
    Date of Patent: June 8, 1993
    Assignee: Boehringer Mannheim GmbH
    Inventors: Fritz Hansske, Otto-Henning Wilhelms, Heidrun Anke
  • Patent number: 5189150
    Abstract: Novel macrolactones with pharmacological effects can be prepared with the aid of Streptoverticillium and Streptomycetes strains.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: February 23, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Axel Zeeck, Siegrid Philipps, Susanne Grabley, Ernold Granzer, Klaus Hutter, Ralf Thiericke, Joachim Wink
  • Patent number: 5183924
    Abstract: Derivatives of benzocycloalkenyldihydroxyalkanoic acids, inhibitors of HMG CoA reductase, antagonists of thromboxane A.sub.2 receptors and antifungals, denoted by the formula I ##STR1## in which X=CH.sub.2, O or S; R.sub.1 and R.sub.2, identical or different, =H, C.sub.1-3 alkyl or together form a --(CH.sub.2).sub.n -- chain (n=4,5) optionally substituted symmetrically by one or two C.sub.1-3 alkyl radicals.R.sub.3 and R.sub.4, identical or different, =H, CF.sub.3, halogen (Cl, F, Br), C.sub.1-5 N,N-dialkylamino, C.sub.1-4 alkyl, C.sub.1-5 -alkoxy, C.sub.1-3 alkylthio, or phenyl optionally substituted by at most substituents which may be identical or different and may denote C.sub.1-3 alkyl or C.sub.1-3 alkoxy radicals or halogens (F, Cl), it being understood that when one of R.sub.3 and R.sub.4 denotes the radicals: CF.sub.3, N,N-dialkylamino, C.sub.6 H.sub.5 or substituted phenyl, it is present at the vertices 3', R' or 5' according to formula 1 and the other denotes a hydrogen atom.R.sub.5 and R.sub.
    Type: Grant
    Filed: October 24, 1991
    Date of Patent: February 2, 1993
    Assignee: Lipha, Lyonnaise Industrielle Pharmaceutique
    Inventors: Didier Festal, Jean-Yves Nioche, Denis Descours, Robert Bellemin, Jacques Decerprit
  • 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
  • Patent number: 5134128
    Abstract: New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.
    Type: Grant
    Filed: May 13, 1991
    Date of Patent: July 28, 1992
    Assignee: Allergan, Inc.
    Inventors: Gary C. M. Lee, Michael E. Garst, John N. Bonfiglio, Elizabeth T. Syage
  • Patent number: 5110954
    Abstract: A process is provided for the production of lactones by the catalytic dehydrogenation of aliphatic diols containing from 3-7 carbon atoms and optionally one or more ether linkages in the diol chain. The reaction is conducted in the liquid phase with a copper chromite catalyst at a temperature of from about 150.degree.-250.degree. C. in the absence of added hydrogen, and preferably at reaction conditions where yields are about 99%.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: May 5, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Harold E. Bellis
  • Patent number: 5110953
    Abstract: Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: ##STR1## wherein R represents C.sub.6 alkyl or alkenyl; and X represents C.sub.2, C.sub.4 or C.sub.6 alkylene or alkenylene; with the provisos that R is C.sub.6 alkyl when X is alkenylene and R is C.sub.6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of:Candida petrophilum, ATCC 20226;Candida oleophila, ATCC 20177;Candida sp., ATCC 20504; andCandida sake, ATCC 28137whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: ##STR2## is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C.sub.9, C.sub.11 or C.sub.
    Type: Grant
    Filed: December 7, 1990
    Date of Patent: May 5, 1992
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, James A. Morris, Mark A. Sprecker, Lynda J. Bienkowski, Kevin P. Miller, Manfred H. Vock, Myrna L. Hagedorn
  • Patent number: 5079372
    Abstract: A method for producing a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic acid ester in the presence of a catalyst, wherein the hydrogenation reaction is conducted in the liquid phase in the presence of (1) ruthenium, (2) an organic phosphine and (3) a compound of a metal selected from the group consisting of Groups IVA, VA and IIIB in the Periodic Table.According to the present invention, for the production of a lactone by hydrogenating a dicarboxylic acid, a dicarboxylic acid anhydride and/or a dicarboxylic ester, the reaction is conducted in a homogeneous liquid phase reaction by using the ruthenium,organic phosphine and compound of a metal selected from the group consisting of Groups IVA, VA and IIIB, of the present invention as the catalyst, whereby the desired lactone product can be obtained at high selectivity under a mild condition as compared with the conventional methods.
    Type: Grant
    Filed: May 1, 1990
    Date of Patent: January 7, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keisuke Wada, Yoshinori Hara, Koushi Sasaki
  • Patent number: 5023347
    Abstract: Described is a process for the preparation of compositions of matter containing unsaturated lactones defined according to the generic structure: ##STR1## wherein R represents C.sub.6 alkyl or alkenyl; and X represents C.sub.2, C.sub.4 or C.sub.6 alkylene or alkenylene; with the provisos that R is C.sub.6 alkyl when X is alkenylene and R is C.sub.6 alkenyl when X is alkylene by means of the sequential steps of (i) fermentation of castor oil or ricinoleic acid using a microorganism selected from the group consisting of:Candida petrophilum, ATCC 20226;Candida oleophila, ATCC 20177;Candida sp., ATCC 20504; andCandida sake, ATCC 28137whereby gamma hydroxydecanoic acid and a mixture of other acids defined according to the generic structure: ##STR2## is formed wherein Y represents an oxo-saturated, oxo-unsaturated or di-unsaturated C.sub.9, C.sub.11 or C.sub.
    Type: Grant
    Filed: June 29, 1990
    Date of Patent: June 11, 1991
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, James A. Morris, Mark A. Sprecker, Lynda J. Bienkowski, Kevin P. Miller, Manfred H. Vock, Myrna L. Hagedorn
  • Patent number: 4962208
    Abstract: A method is improved for producing highly stable non-pyrogenic solutions of magnesium gluconocitrate. According to this process a specially prepared non-pyrogenic magnesium hydroxycarbonate or magnesium carbonate, gluconic acid anhydride and citric acid are first admixed to form a powder. The admixed powder is then added to an aqueous medium and heated to a temperature of at least about 80.degree. C. to rapidly drive out substantially all of the carbon dioxide. Alternatively, the aqueous medium may be heated to a temperature of at least 80.degree. C. prior to the addition of the powder. The magnesium hydroxycarbonate or magnesium carbonate is prepared by heating to 165.degree. C. for about 18 hours in thin layers in the presence of steam and an oxidizing atmosphere whereby any and all traces of organic material which could be pyrogen forming is eliminated by oxidation thereof.
    Type: Grant
    Filed: January 6, 1989
    Date of Patent: October 9, 1990
    Inventor: Alfred R. Globus
  • Patent number: 4940726
    Abstract: The isolation and elucidation of novel caffrane macrocyclic lactones denominated "Combretastatin D-1" and "Combretastatin D-2", each of which was found to possess unexpected cell growth inhibitory properties.
    Type: Grant
    Filed: April 26, 1989
    Date of Patent: July 10, 1990
    Assignee: Arizona Board of Regents
    Inventors: George R. Pettit, Sheo B. Singh
  • Patent number: 4709058
    Abstract: The catalytic thermal depolymerization of polyesters to produce macrocyclic esters suitable for fragrance applications is carried out using an olefin polymer. High yields of the corresponding macrocyclic ester are produced at high rates while substantially eliminating reactor fouling and the formation of undesirable by-products. The depolymerization is most advantageously conducted using polyethylene.
    Type: Grant
    Filed: September 19, 1986
    Date of Patent: November 24, 1987
    Assignee: National Distillers and Chemical Corporation
    Inventors: Joseph Cahill, Jr., Herbert G. Rodenberg
  • Patent number: 4703128
    Abstract: The feature of the present invention is a process for preparing compounds represented by general formula (Ia) described below: ##STR1## wherein X.sub.1, X.sub.2, X.sub.3, R.sub.1, R.sub.2, R.sub.3 and R.sub.7 are as defined in formula (I) and R.sub.10 represents a lower alkyl group, or acid salts thereof, which process is characterized by using the guanidylfungins (II) as raw materials, reacting these guanidylfungins with alcohols (III) in the presence of an acid catalyst, and then hydrolyzing the malonic acid monoester (IV).
    Type: Grant
    Filed: July 18, 1986
    Date of Patent: October 27, 1987
    Assignee: Takahara Shuzo Co., Ltd.
    Inventors: Teruhiko Beppu, Kazutoh Takesako, Teruya Nakamura, Akira Obayashi
  • Patent number: 4602114
    Abstract: A process for the production of .epsilon.-caprolactone wherein 4-penten-1-ol is reacted carbon monoxide in the presence of a ligand-stabilized Pd(II) catalyst complexed with a Group IVB metal halide.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: July 22, 1986
    Assignee: Phillips Petroleum Company
    Inventors: Michael S. Matson, Gerald R. Kahle
  • Patent number: 4594434
    Abstract: Dawsonite is a highly effective and useful catalyst for the thermal depolymerization of polyesters to produce macrocyclic compounds. High yields and enhanced rates of reaction are obtained using Dawsonite obtained from natural or synthetic sources.
    Type: Grant
    Filed: November 5, 1984
    Date of Patent: June 10, 1986
    Assignee: National Distillers and Chemical Corporation
    Inventors: Joseph Cahill, Jr., Eugene G. Harris
  • Patent number: 4568470
    Abstract: Described for use in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes and perfumed articles, foodstuffs, chewing gums, toothpastes and medicinal products are the cis and/or trans isomers of the macrocyclic lactone defined according to the structure: ##STR1## produced according to the process of first reacting the ester defined according to the structure: ##STR2## with the alkenol having the structure: ##STR3## in order to produce the di-unsaturated ester having the structure: ##STR4## and then causing the said diester to undergo an internal metathesis to form the compound having the structure: ##STR5##
    Type: Grant
    Filed: January 15, 1985
    Date of Patent: February 4, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Augustinus G. Van Loveren, Marie R. Hanna, Domenick Luccarelli, Jr., David R. Bowen, Manfred H. Vock, Wilhelmus J. Wiegers
  • Patent number: 4499288
    Abstract: A process is provided for the thermal depolymerization of polyesters to produce macrocyclic compounds utilizing mixed-metal catalysts. Useful mixed-metal catalysts consist of an aluminum alkoxide or aluminum carboxylate with an alkali metal or magnesium alkoxide or carboxylate, or double metal salts thereof. High yields and enhanced rates of reaction are obtained using the mixed-metal catalysts of this invention.
    Type: Grant
    Filed: June 6, 1983
    Date of Patent: February 12, 1985
    Assignee: National Distillers and Chemical Corporation
    Inventor: Eugene G. Harris
  • Patent number: 4393223
    Abstract: Mixed metal compounds comprised of aluminum alkoxides or aluminum carboxylates with an alkali metal or magnesium alkoxide or carboxylate are useful catalysts for the thermal depolymerization of polyesters to produce macrocyclic compounds. High yields and enhanced rates of reaction are possible utilizing these mixed metal catalysts in known depolymerization procedures.
    Type: Grant
    Filed: July 22, 1981
    Date of Patent: July 12, 1983
    Assignee: Emery Industries, Inc.
    Inventor: Eugene G. Harris
  • Patent number: 4385065
    Abstract: There is disclosed a novel series of compounds isolated from the fermentation broth of a strain of the microorganism Streptomyces sp MA5038. The compounds have a 16-membered macrocyclic lactone structure with various substituents thereon. The compounds have insecticidal and antitapeworm activity and compositions for such uses are disclosed.
    Type: Grant
    Filed: October 5, 1981
    Date of Patent: May 24, 1983
    Assignee: Merck & Co., Inc.
    Inventors: George E. Albers-Schonberg, Sebastian Hernandez, Leeyuan Huang
  • Patent number: 4363922
    Abstract: Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.
    Type: Grant
    Filed: June 15, 1981
    Date of Patent: December 14, 1982
    Assignee: The Upjohn Company
    Inventors: Barney J. Magerlein, Howard A. Whaley
  • Patent number: 4360682
    Abstract: Caprolactones such as .epsilon.-caprolactone are stabilized against discoloration with dihydroxybenzenes such as hydroquinone or compounds of the formula ##STR1## in which R.sub.1 is alkyl of 1 to 8 carbon atoms, andR.sub.2 is hydrogen or alkyl of 1 to 8 carbon atoms.Even the presence of air is not detrimental.
    Type: Grant
    Filed: May 12, 1980
    Date of Patent: November 23, 1982
    Assignees: Deutsche Gold- und Silberscheideanstalt vormals Roessler, Bayer Aktiengesellschaft
    Inventors: Herbert Klenk, Rolf Wirthwein, Helmut Waldmann, Hermann Seifert
  • Patent number: 4360683
    Abstract: Novel antibacterially-active esters of antibiotic nodusmicin. Activity is demonstrated against Staphylococcus aureus, Streptococcus pyogenes, and Sarcina lutea. Thus, these esters can be used in various known environments, using well-known procedures, to eradicate or control susceptible microbes.
    Type: Grant
    Filed: August 6, 1980
    Date of Patent: November 23, 1982
    Assignee: The Upjohn Company
    Inventors: Barney J. Magerlein, Howard A. Whaley
  • Patent number: 4331603
    Abstract: A process is provided whereby the malodorous and undesirable constituents present with macrocyclic fragrance compounds obtained by the thermal depolymerization of polyesters are removed. The process involves contacting the macrocyclic compound maintained in a liquid state with ozone or ozone and an aqueous solution of hydrogen peroxide.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: May 25, 1982
    Assignee: Emery Industries, Inc.
    Inventor: Eugene G. Harris