The Lactone Ring Is Five-membered Patents (Class 549/295)
  • Patent number: 5646307
    Abstract: A process for the preparation of .gamma.-butyrolactone, in which 2,5-dihydrofuran or 2,3-dihydrofuran or a mixture of these two dihydrofurans is caused to react in the gas phase in the presence of water and in the presence or absence of additional hydrogen at elevated temperature over a hydrogenating catalyst.
    Type: Grant
    Filed: May 16, 1996
    Date of Patent: July 8, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Pinkos, Rolf Fischer
  • 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: 5596015
    Abstract: Compounds having formula (3), wherein R.sup.1 is hydrogen, straight or branched alkyl with 1-10 carbon atoms, straight or branched alkenyl with 2-10 carbon atoms, straight or branched alkynyl with 2-10 carbon atoms, benzyl or aryl, optionally mono- or plurisubstituted with straight or branched alkyl with 1-10 carbon atoms, hydroxy, alkoxy, halogen, an amino or a nitro group; and when R.sup.1 is H salts thereof, or R.sup.1 is acyl (R.sup.1 =--COR.sup.2) wherein R.sup.2 is straight or branched alkyl with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms, alkynyl with 2-10 carbon atoms, or aryl, optionally mono- or plurisubstituted with alkyl with 1-10 carbon atoms, hydroxy, alkoxy, halogen, an amino or a nitro group. Compounds of formula (3) have interesting antifungal activities and may, accordingly, be used as active ingredients in fungicidal compositions.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: January 21, 1997
    Assignee: Novo Nordisk A/S
    Inventors: Jens Breinholt, Lene Lange
  • Patent number: 5527364
    Abstract: An alkylphenoxypolyoxyalkylene amine lactone composition obtained by reacting:(a) a lactone represented by the formula: ##STR1## where n is a number between about 1 and about 5; and (b) an alkylphenoxypolyoxyalkylene amine represented by the formula: ##STR2## in which R' is a hydrocarbyl radical having from about 4 to 30 carbon atoms, x represents a number from about 5 to 50, and R" represents a C.sub.2 -C.sub.5 hydrocarbyl radical or any combination of C.sub.2 -C.sub.5 hydrocarbyl radicals, such that the oxyalkylene radical can comprise any combination of repeating C.sub.2 -C.sub.5 oxyalkylene units to form block or random copolymers.
    Type: Grant
    Filed: July 31, 1995
    Date of Patent: June 18, 1996
    Assignee: Texaco Inc.
    Inventors: Joseph M. Russo, Thomas F. DeRosa, Benjamin J. Kaufman
  • Patent number: 5502075
    Abstract: Leukotriene-B.sub.4 derivatives of formula I ##STR1## their salts with physiologically compatible bases and their cyclodextrin clathrates are described.
    Type: Grant
    Filed: May 27, 1994
    Date of Patent: March 26, 1996
    Assignee: Schering Aktiengesellschaft
    Inventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Fro/ hlich, Roland Ekerdt, Claudia Giesen
  • 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: 5480893
    Abstract: The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras.
    Type: Grant
    Filed: May 13, 1994
    Date of Patent: January 2, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Samuel L. Graham, S. Jane deSolms
  • Patent number: 5478803
    Abstract: Described are 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures defined according to the structure: ##STR1## wherein structure represents mixtures wherein in the mixture in each of the compounds, one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond, processes for preparing same and uses thereof in augmenting or enhancing the aroma of consumable materials including perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers). Also described is a process for preparing such 3,5-dimethyl-pentenyl-dihydro-2(3H)-furanone isomer mixtures using as a starting material 2,7-octadienol having the structure: ##STR2## as well as the process intermediates having the structures: ##STR3## wherein R represents C.sub.1 -C.sub.4 alkyl; R.sub.1 and R.sub.
    Type: Grant
    Filed: October 27, 1994
    Date of Patent: December 26, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William J. Fylak, Marie R. Hanna, Futoshi Fujioka
  • Patent number: 5474995
    Abstract: The invention encompasses the novel compound of Formula I useful in the treatment of cyclooxygenase-2 mediated diseases, ##STR1## The invention also encompasses certain pharmaceutical compositions for treatment of cyclooxygenase-2 mediated diseases comprising compounds of Formula I.
    Type: Grant
    Filed: January 10, 1994
    Date of Patent: December 12, 1995
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Yves Ducharme, Jacques Y. Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyin Wang, Serge Leger, Michel Therien
  • Patent number: 5468881
    Abstract: After the lactone portion of trans-whiskey lactone is hydrolyzed with potassium hydroxide, this portion is reacted with isopropyl bromide and mixed with an alkyl group, thereby obtaining isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate. Then, the isopropyl (3S,4S)-4-hydroxy-3-methyloctanoate is reacted with diethyl azodicarboxylate in the presence of triphenylphosphine and azodicarboxylate, thereby obtaining isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate. The isopropyl (3S,4S)-4-(3',5'-dinitrobenzoyloxy)-3-methyloctanoate is hydrolyzed in 2% potassium hydroxide, and as a result, cis-whiskey lactone (A) represented by the following general formula is obtained. According to this method, cis-whiskey lactone, one of the perfume components of whiskey and wine, can be produced selectively and easily.
    Type: Grant
    Filed: August 27, 1992
    Date of Patent: November 21, 1995
    Assignees: Japan Tobacco Inc., Yuji Gosei Kogyo Co., Ltd.
    Inventors: Takashi Ebata, Katsuya Matsumoto, Koshi Koseki, Hiroshi Kawakami, Hajime Matsushita, Hajime Yoshikoshi, Masakazu Okaniwa
  • Patent number: 5462694
    Abstract: A mesomorphic compound of the formula (I) according to claim 1 characterized by having at least one cyclic group selected from .beta. class including, e.g., thiazole-2,5-diyl, benzoxazole-2,5-diyl, indan-2,5-diyl, and quinoxaline-2,6-diyl and also having a linkage of Y.sup.1 (CH.sub.2).sub.m Y.sup.2, where Y.sup.1 and Y.sup.2 are --CH.sub.2 --, --O--, --COO-- or --OCO-- and m is 1-16, is suitable as a component for a liquid crystal composition providing improved response characteristics. A liquid crystal device is constituted by disposing the liquid crystal composition between a pair of substrates. The liquid crystal device is used as a display panel constituting a liquid crystal apparatus providing good display characteristics.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: October 31, 1995
    Assignee: Canon Kabushiki Kaisha
    Inventors: Yoko Kosaka, Takao Takiguchi, Takashi Iwaki, Takeshi Togano, Shinichi Nakamura, Ikuo Nakazawa
  • Patent number: 5453516
    Abstract: A process for preparing 5-membered ring heterocycles of the general formula I ##STR1## where R.sup.1 is methyl or hydroxyethyl,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are hydrogen, C.sub.1 - to C.sub.12 -alkyl, C.sub.2 - to C.sub.12 -alkenyl, aryl, C.sub.3 - to C.sub.8 -cycloalkyl, C.sub.1 - to C.sub.12 -alkoxy, halogen, C.sub.2 - to C.sub.20 -alkoxycarbonylalkyl, C.sub.2 - to C.sub.20 -alkylcarbonyloxy, formyl, C.sub.2 - to C.sub.20 -formylalkyl, benzoyl or --CH(OR.sup.3)(OR.sup.5), or R.sup.3 and R.sup.5 together are a C.sub.2 - to C.sub.7 -alkylene chain which is unsubstituted or monosubstituted to pentasubstituted by R.sup.4 or a .dbd.CH--CH.dbd.CH--CH.dbd. unit which is unsubstituted or monosubstituted to tetrasubstituted by R.sup.4,X is oxygen or N--R.sup.4by reacting 5-membered ring heterocycles of the general formula II ##STR2## where R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and X have the abovementioned meanings and Y is hydrogen, acetyl or C.sub.2 - to C.sub.
    Type: Grant
    Filed: December 13, 1993
    Date of Patent: September 26, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Rolf Pinkos
  • Patent number: 5449823
    Abstract: Two optically active forms of 4-hydroxy-3-methyl-2-keto-pentanoic acid of the formula ##STR1## wherein carbon atom 4 has the (S)-configuration, and carbon atom 3 can have the (R)-configuration or the (S)-configuration (compound I) are made using a biotransformation process. Compound I may be manufactured by reacting 4-hydroxy-isoleucine (2S, 3R, 4S) of the formula: ##STR2## with microorganisms which have L-amino acid oxidase activity or with an L-amino acid oxidase. Compound I is a flavor precursor and may also be used as an intermediate for the production of the optically active (5S)-3-hydroxy-4,5-dimethyl-2(5H)-furanone: ##STR3## which is useful as a flavorant.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: September 12, 1995
    Assignee: Givaudan-Roure Corporation
    Inventor: Konrad Lerch
  • Patent number: 5447954
    Abstract: Compounds of the formula ##STR1## where the substituents are defined in the specification useful in the treatment of hyperlipidemia.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: September 5, 1995
    Assignee: SmithKline Beecham p.l.c.
    Inventors: Andrew D. Gribble, Pieter H. E. Groot, Antony N. Shaw, Roland E. Dolle
  • 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: 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: 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: 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: 5401857
    Abstract: A cyclocarbonylation process for making .gamma.-butyrolactones under mild temperature and pressure conditions is disclosed. In the process, an allylic alcohol reacts with carbon monoxide in the presence of a rhodium carbonyl catalyst and an amount of a pyridine promoter effective to enhance the selectivity of the process for making the .gamma.-butyrolactone product. The process provides a way of making .gamma.-butyrolactone from allyl alcohol as the only C4 product.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: March 28, 1995
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Roger A. Grey, Diandre Armstead
  • Patent number: 5376676
    Abstract: 4-(C.sub.10 -C.sub.20)alkyl-2(5H)-furanone compounds are selective calcium channel inhibitors and useful for treatment of diseases such as hypertension, angina, cardiac arrythmia, pulmonary hypertension, aortic insufficiency, Raynand's disease, migraine headaches, deficiency of platelet function, atherosclerosis, ischemia, reprofusion injury, bronchial asthma, esophageal spasm, dysmenorhea, allergic contact dermatitis, acute inflammatory response, glaucoma and as potentiators of chemotherapeutic agents in the treatment of tumors.
    Type: Grant
    Filed: August 30, 1991
    Date of Patent: December 27, 1994
    Assignee: Allergan, Inc.
    Inventor: Gary C. M. Lee
  • Patent number: 5374744
    Abstract: An alkynyl group having a triple bond at the carbon atom at the 1-position is introduced to a carbon atom at the 1-position of 2,3-O-isopropylidene-D-ribofuranose. The diol part is then cleaved to obtain a lactol compound. This lactol compound is oxidized to obtain a lactone compound. The ketal part of the lactone compound is hydrolyzed and the compound is further subjected to a reduction reaction. The hydroxyl groups at the 2- and 3-positions are then eliminated, and the double bond between the 2- and 3-positions of the resultant compound is reduced to obtain a 4-substituted-.gamma.-lactone.
    Type: Grant
    Filed: October 21, 1992
    Date of Patent: December 20, 1994
    Assignees: Japan Tobacco Inc., Fuji Flavor Co., Ltd.
    Inventors: Koshi Koseki, Hiroshi Kawakami, Takashi Ebata, Hajime Matsushita, Mikio Ono
  • Patent number: 5371106
    Abstract: Compounds based on 3,4-diaryl-(5H)-furan-2-one, with fungicidal activity, having the general formula (I): ##STR1##
    Type: Grant
    Filed: March 24, 1993
    Date of Patent: December 6, 1994
    Assignee: Ministero dell'Universita' e della Ricerca Scientifica e Technologica
    Inventors: Giovanni Camaggi, Lucio Filippini, Marilena Gusmeroli, Raul Riva, Carlo Garavaglia, Luigi Mirenna
  • Patent number: 5358964
    Abstract: The manufacture and use of compounds of the formula ##STR1## wherein Y is O or S, R.sub.1 is hydrogen or alkyl, and R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen or various substituent groups, and pharmaceutically acceptable acid addition salts thereof. The compounds have activity as inhibitors of the IL-I or other agonist-induced proteoglycan degradation in bovine nasal cartilage and pharmaceutical compositions containing such compounds are described to treat conditions advantageously affected by such inhibition including arthritis.
    Type: Grant
    Filed: July 26, 1993
    Date of Patent: October 25, 1994
    Assignee: Warner-Lambert Company
    Inventors: Vijaykumar Baragi, Diane H. Boschelli, David T. Connor, Richard R. Renkiewicz
  • Patent number: 5336686
    Abstract: A compound selected from the group consisting of a compound of the formula ##STR1## wherein the substituents are defined as in the application having antiglucocorticoid and antiprogestomimetic properties and a process and intermediates for their preparation.
    Type: Grant
    Filed: February 19, 1993
    Date of Patent: August 9, 1994
    Assignee: Roussel-Uclaf
    Inventors: Lucien Nedelec, Francois Nique, Daniel Philibert
  • Patent number: 5322942
    Abstract: Optically active lactones are described, such as an intermediate lactone having the formula ##STR1## where R and R.sup.2 are each independently alkyl with 1 to 6 carbon atoms, cycloalkyl with 6 to 10 carbon atoms, aryl with 6 to 10 carbon atoms, or arylalkyl with 7 to 19 carbon atoms, R.sup.4 is H or C.sub.1-6 alkyl, and Ar is a homo- or heteroaromatic ring with 5 or 6 ring atoms being optionally substituted by C.sub.1-6 alkyl or alkoxy groups, halogen atoms, cyano or nitro groups. Such optically active, intermediate lactones are prepared from L-aspartic acid, and can be readily converted to (+)-pilocarpine and its analogues by hydrolysis, reduction, and hydrogenation, such as to an optically active lactone having the formula ##STR2## which is (+)-pilocarpine when R is ethyl, R.sup.4 is H, and Ar is 1-methylimidazol-5-yl.
    Type: Grant
    Filed: June 3, 1991
    Date of Patent: June 21, 1994
    Assignee: Regents of the University of California
    Inventors: Henry Rapoport, Jeffrey M. Dener, Lin-hau Zhang
  • Patent number: 5319108
    Abstract: A method for producing (R,Z)-5-tetradecen-4-olide, comprising the following reaction formulas; ##STR1##
    Type: Grant
    Filed: October 25, 1991
    Date of Patent: June 7, 1994
    Assignees: Japan Tobacco Inc., Fuji Flavor Co., Ltd.
    Inventors: Takashi Ebata, Hiroshi Kawakami, Koshi Koseki, Hajime Matsushita, Mikio Ono
  • 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: 5308540
    Abstract: Liquid crystalline compounds having an optionally active .gamma.-lactone ring of the formula: ##STR1## wherein R.sup.1 is a group selected from the group 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; R.sup.2 is a group of the formula: --(CO).sub.m --R.sup.4 ; m is 0 or 1; R.sup.4 is hydrogen atom or an alkyl having 1 to 15 carbon atoms; and the symbol * is an asymmetric carbon atom, and an intermediate thereof, and process for the production of the same.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: May 3, 1994
    Assignee: Daiso Co., Ltd.
    Inventors: Kazuhiko Sakaguchi, Naoya Kasai, Yoshikazu Takehira, Tohru Kitamura, Yutaka Shiomi
  • Patent number: 5288811
    Abstract: Accordingly, novel carbonyl containing compositions are prepared by contacting, in the presence of a free radical initiator, a compound selected from the group consisting of saturated hydrocarbons, substituted saturated hydrocarbons, polymers and mixtures thereof with a carbonyl containing compound or mixtures thereof having the structures: ##STR1## wherein Q.dbd.HOH, MeOH, EtOH, or n-BuOH; n.dbd.0,1,>; and X and Y are independently selected from the group consisting of CH.sub.2, C.dbd.O; W is independently selected from the group consisting of CH.sub.2, C.dbd.O, O, NH, CMe.sub.2, C.dbd.N-alkyl and N-alkyl, wherein alkyl is 1 to 18 carbons; U and V are independently selected from the same groups as W and dependently selected so that U and V taken together are one of 1,2-phenylene, 1,8-naphthalene-diyl, and 1,2-naphthalene-diyl.
    Type: Grant
    Filed: November 5, 1992
    Date of Patent: February 22, 1994
    Assignee: Exxon Research and Engineering Company
    Inventor: Stanley J. Brois
  • 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: 5274128
    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 ramanniana var. ramanniana--CBS 112.08Mortierella ramanniana var. ramanniana--CBS 478.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: December 28, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, Lynda B. McLean, James A. Morris, Henry A. Bondarovich
  • 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: 5216177
    Abstract: First, levoglucosenone is made to react with methyl lithium in the presence of copper iodide in order to introduce a methyl group into an enone group of levoglucosenone, and to obtain 1,6-anhydro-3,4-dideoxy-4-C-methyl-.beta.-D-erythro-hexopyranose-2-ulose. This methyl compound is oxidized in acetic acid for lactone formation, and (3S,4S)-5-hydroxy-3-methylpentan-4-olide is thus obtained. Further, this lactone is made to react with tosyl chloride in anhydrous pyridine to obtain (3S,4S)-3-methyl-5-tosyloxypentan-4-olide (tosylate). The obtained tosylate is alkylated with n-propyl lithium in the presence of copper iodide to obtain (3S,4R)-3-methyl-4-octanolide. Here, the (3S,4S)-3-methyl-5-tosyloxypentan-4-olide may be treated with potassium carbonate to cleave lactone ring once, thereby obtaining epoxide. After that, the obtained epoxide is alkylated to form lactone ring again to obtain (3S,4R)-3-methyl-4-octanolide.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: June 1, 1993
    Assignee: Japan Tobacco Inc.
    Inventors: Takashi Ebata, Hajime Matsushita, Hiroshi Kawakami, Koshi Koseki
  • Patent number: 5210229
    Abstract: Gamma-butyrolactone is prepared by catalytic dehydrogenation of 1,4-butanediol in a gaseous phase in the presence of a catalyst comprising copper, chromium, and manganese and/or barium. Improvement is in that the catalyst further contains sodium and/or potassium, whereby formation of by-products is suppressed and high yield, high selectivity and prolonged catalyst life are attained.
    Type: Grant
    Filed: July 16, 1992
    Date of Patent: May 11, 1993
    Assignee: Tonen Chemical Corporation
    Inventors: Tatsumi Ichiki, Kaori Mori, Sadakatsu Suzuki, Hiroshi Ueno, Kenji Kobayashi
  • Patent number: 5189182
    Abstract: 5-Methylbutyrolactone is prepared by a process in which a pentenoic ester of the formula IX--CO.sub.2 R (I),where X is CH.sub.2 .dbd.CH--CH.sub.2 --CH.sub.2 --, CH.sub.3 --CH.dbd.CH--CH.sub.2 -- or CH.sub.3 --CH.sub.2 --CH.dbd.CH-- and R is alkyl, cycloalkyl, aralkyl or aryl, or a mixture of these esters is reacted with water at from 50.degree. to 350.degree. C. in the presence or absence of a diluenta) over a zeolite and/or phosphate catalyst orb) in the presence of from 0.01 to 0.25 mole of a sulfonic acid, a Lewis acid and/or a non-oxidizing mineral acid per mole of pentenoic ester or over from 0.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: February 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Heinz-Walter Schneider, Werner Bertleff, Rolf Fischer, Uwe Vagt, Fritz Naeumann, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 5183908
    Abstract: This invention relates to an improved process for the preparation of 3-acyl-5-alkyldihydro-2(3H)-furanones according to the following reaction scheme: ##STR1## wherein R and R.sub.1 are hydrogen or alkyl and R.sub.2 is a hydrocarbon or -O-hydrocarbon radical of from 1 to 20 carbon atoms and X is a leaving group.
    Type: Grant
    Filed: February 27, 1990
    Date of Patent: February 2, 1993
    Assignee: Henkel Corporation
    Inventors: A. Frederick Elsasser, Thomas J. Korte
  • Patent number: 5179077
    Abstract: The invention concerns the novel compound, 4-methyl-3-pentyl-2 (5H)-furanone, I, a process for the manufacture of I and fragrance and flavor compositions containing I.
    Type: Grant
    Filed: September 27, 1991
    Date of Patent: January 12, 1993
    Assignee: Givaudan Corporation
    Inventors: Peter M. Muller, Hans-Jakob Wild
  • 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: 5164499
    Abstract: Nitroaryl carbonyl Formula (IIA) compounds, their nitrodihydroaryl carbonyl Formula (I) intermediates, processes for preparing Formula (II) compounds, and a process for preparing Formula (I) compounds, wherein each process comprises the reaction of a nitroaryl compound with a silane.
    Type: Grant
    Filed: January 2, 1990
    Date of Patent: November 17, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thaliyil V. Rajanbabu
  • 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: 5130157
    Abstract: The present invention relates to a process for obtaining an aroma concentrate that is enriched in lactones. The present invention is particularly concerned with a process for concentrating lactones from a distillate obtained by the distillative deacidification of a fat composition rich in lauric acid residues, said distillate containing at least 0.1 wt. % of lactones having 6-20 carbon atoms, by subjecting the distillate or a fraction thereof to a fractional distillation so as to obtain a fraction containing at least 1 wt. % of lactones having 6-20 carbon atoms.The present invention offers a commercially and technically attractive route for obtaining natural lactones.Other aspects of the present invention are a lactone concentrate obtainable by the above process, the use of such a concentrate for flavoring food products and to food products flavored by such a lactone concentrate.
    Type: Grant
    Filed: January 23, 1991
    Date of Patent: July 14, 1992
    Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.
    Inventors: Franciscus H. Hulsker, Koene de Jong, Hessel Turksma
  • Patent number: 5128370
    Abstract: New furans and lactones from streptomycetes, a process for the preparation thereof, and the use thereof.It is possible with the aid of various streptomycetes species to prepared new compounds having a furan or lactone structure. These compounds have a pharmacological, especially antibiotic, action.
    Type: Grant
    Filed: March 20, 1989
    Date of Patent: July 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Susanne Grabley, Joachim Wink, Klaus Kuhlein, Gerhard Seibert, Klaus Hutter, Hermann Uhr, Axel Zeeck
  • Patent number: 5114493
    Abstract: This invention provides smoking compositions which contains a 6-substituted hexahydrobenzofuranone flavorant additive.Under cigarette smoking conditions the flavorant additive enhances the aroma and flavor of the cigarette smoke.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: May 19, 1992
    Assignees: Philip Morris Inc., Philip Morris Products Inc.
    Inventor: Kenneth F. Podraza
  • 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: 5106995
    Abstract: A method for converting 1,4 and 1,5 aliphatic saturated diols to lactones is disclosed wherein the diol is reacted with a chemical oxidizing agent and a ruthenium containing catalyst at temperatures substantially less than 200.degree. C. The reaction proceeds quickly and produces high yields of the desired product.
    Type: Grant
    Filed: May 5, 1989
    Date of Patent: April 21, 1992
    Assignee: ISP Investments Inc.
    Inventor: Jeffrey S. Plotkin
  • Patent number: 5059611
    Abstract: New 5-hydroxy-2-furanone compounds have anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: October 22, 1991
    Assignee: Allergan, Inc.
    Inventor: Gary C. M. Lee
  • Patent number: 5045564
    Abstract: New 2-furanone compounds have calcium channel antagonist activity and are useful as anti-inflammatory agents and in treating psoriasis.
    Type: Grant
    Filed: October 25, 1989
    Date of Patent: September 3, 1991
    Assignee: Allergan, Inc.
    Inventor: Gary C. M. Lee
  • Patent number: 5030328
    Abstract: A method of separating .gamma.-butyrolactone from a mixture containing ethanol, tetrahydrofuran, water, n-butanol, 1,4-butanediol, diethyl succinate and .gamma.-butyrolactone, by distillation in vacuum columns.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: July 9, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Rolf Fischer, Peter Stops, Erwin Brunner, Rudolf Weigand
  • 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