Additional Chalcogen Bonded Directly To The Lactone Ring Patents (Class 549/313)
  • Patent number: 4874782
    Abstract: This invention provides certain furanone derivatives, their pharmaceutical formulations, and their use in a method for treating inflammation, asthma, or allergies.
    Type: Grant
    Filed: June 26, 1987
    Date of Patent: October 17, 1989
    Assignee: Eli Lilly and Company
    Inventors: Rosanne Bonjouklian, Christopher J. M. Meade, Edward D. Mihelich, Michael L. Phillips
  • Patent number: 4855320
    Abstract: The present invention provides 5-arylalkyl-4-alkoxy-2(5H)-furanones of the formula: ##STR1## wherein the oxygen atoms on C-5 and C-.alpha., relative to one another, are in the threo-position, with the exclusion of those compounds of the formula (I) wherein R.sup.2 is H or CH.sub.3 when n=0 or 2, R.sup.o =H, R.sup.1 =CH.sub.3, R.sup.3 =H and R.sup.4 =H.The present invention also provides processes for their preparation, as well as new 3-alkoxy-5-(subst.)-phenyl-2(E), 4(E)-pentadienoates as reactive intermediates for the preparation of the new furanone derivatives.The new furanone derivatives of the threo series are active as anticonvulsives/anti-epileptics. Therefore, the present invention also provides medicaments which contain these new furanone derivatives, as well as known furanones, the anticonvulsive/anti-epileptic effectiveness of which has been found for the first time.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: August 8, 1989
    Assignee: Dr. Willmar Schwabe GmbH & Company
    Inventors: Shyam S. Chatterjee, Klaus Klessing
  • Patent number: 4851540
    Abstract: Process for the production of imidazole derivatives of the formula: ##STR1## wherein R.sub.1 is an (R)- or (S)-1-phenylalkyl group, an (R)- or (S)-1-alkoxycarbonyl-1-phenylmethyl group or an (R)- or (S)-1-aryloxycarbonyl-1-phenylmethyl group, R.sub.2 is hydrogen, a substituted or unsubstituted alkanoyl group, an unsubstituted or a substituted benzoyl group, a substituted or an unsubstituted benzyl group, an alkoxycarbonyl group, and aryloxycarbonyl group, an alkoxyalkyl group, a pyranyl group, a substituted or unsubstituted benzenesulfonyl group, an alkylsulfonyl group, a diarylphosphinyl group, a dialkoxyphosphinyl group or a trialkylsilyl group, and A is a sulfur or oxygen atom.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: July 25, 1989
    Assignee: Lonza Ltd.
    Inventors: John McGarrity, Leander Tenud, Thomas Meul
  • Patent number: 4843093
    Abstract: Butyrolactone derivatives having the formula ##STR1## wherein R is a C.sub.4 -C.sub.10 alkyl group, which have an appetite-regulating effect, a process for their production, and compositions containing them, are disclosed.
    Type: Grant
    Filed: May 29, 1987
    Date of Patent: June 27, 1989
    Assignee: Ajinomoto Co., Inc.
    Inventors: Yoichiro Nagai, Taichi Nakano, Yutaka Oomura
  • Patent number: 4822897
    Abstract: Polyfluoro .gamma.-ketoester compounds are obtained by reaction of ethylenic monoolefins, a metal or quaternary ammonium cyanide, and a fluoroester. These compounds, which have a general formula R.sub.F C(O)CFYCF.sub.2 CO.sub.2 R.sup.1, can be copolymerized directly with fluorinated ethylenic monoolefins, or further reacted to form vinyl ether and allyl ether derivatives which may also be copolymerized with ethylenic comonomers, forming solid, moldable copolymers with useful properties determined by the nature of pendant functional groups R.sub.F.
    Type: Grant
    Filed: June 3, 1987
    Date of Patent: April 18, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4801723
    Abstract: A process for the preparation of compounds of the (1RS, 4RS, 5SR), (1R, 4R, 5S) or (1S, 4S, 5R) configuration having the formula ##STR1## wherein Y is selected from the group consisting of hydrogen and the organic residue Z of an optionally chiral alcohol of the formula ZOH comprising reacting in the presence of an acid agent 5RS-hydroxy-2,5-dihydrofuran-2-one having the formula ##STR2## either (a) with an achiral alcohol of the formula ZOH to obtain the resulting ether and reacting the latter in an anhydrous medium with an isopropylidene sulfurane of the formula ##STR3## wherein R.sub.1 and R.sub.
    Type: Grant
    Filed: April 10, 1987
    Date of Patent: January 31, 1989
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre DeMoute
  • Patent number: 4797417
    Abstract: The invention relates to novel furanone derivatives, having an aldose reductase-inhibitory activity, of the formula ##STR1## wherein A is a lower alkylene group,R.sup.1 is a carboxy, hydroxy, protected hydroxy or lower alkoxycarbonyl group,R.sup.2 is a hydrogen or halogen atom or a halo (lower) alkyl group, andR.sup.3 is a hydrogen atom or a hydroxy, carboxy, lower alkoxy or lower alkoxycarbonyl group.
    Type: Grant
    Filed: March 27, 1987
    Date of Patent: January 10, 1989
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masanori Okamoto, Itsuo Uchida, Kazuyoshi Umehara, Masanobu Kohsaka, Hiroshi Imanaka
  • Patent number: 4789749
    Abstract: Analogs of the marine natural product manoalide are useful in treating mammals, including humans, in need of a drug having analgesic/anti-inflammatory, immunosuppressive, and/or antiproliferative activity.
    Type: Grant
    Filed: February 19, 1986
    Date of Patent: December 6, 1988
    Assignee: The Regents of the University of California
    Inventors: Robert S. Jacobs, D. John Faulkner
  • Patent number: 4686300
    Abstract: Polyfluoro .gamma.-ketoester compounds are obtained by reaction of ethylenic monoolefins, a metal or quaternary ammonium cyanide, and a fluoroester. These compounds, which have a general formula R.sub.F C(O)CFYCF.sub.2 CO.sub.2 R.sup.1, can be copolymerized directly with fluorinated ethylenic monoolefins, or further reacted to form vinyl ether and allyl ether derivatives which may also be copolymerized with ethylenic comonomers, forming solid, moldable copolymers with useful properties determined by the nature of pendant functional groups R.sub.F.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: August 11, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 4585789
    Abstract: Described are compounds of the formula: ##STR1## Wherein A is a lower alkylene group;R.sup.1 is a carboxy, hydroxy, lower alkoxycarbonyl, lower alkoxycarbonylamino, phenyl(lower)alkyloxy, benzoyloxy or lower alkanoyloxy group;R.sup.2 is a hydrogen or halogen atom or a halo(lower)alkyl group;R.sup.3 is a hydrogen or halogen atom;R.sup.4 is hydroxy, lower alkoxy, lower alkanoyloxy or lower alkoxycarbonyloxy group; andR.sup.5 is a hydrogen or halogen atom;Q is the number of double bonds which is equal to 0 or 1;n is an integer of 0 or 1, provided that when Q is 0, n is 1 and when Q is 1, n is 0.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: April 29, 1986
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masanori Okamoto, Itsuo Uchida, Kazuyoshi Umehara, Masanobu Kohsaka, Hiroshi Imanaka
  • Patent number: 4556732
    Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the production of numerous esters having elevated insecticidal activity.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: December 3, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4526988
    Abstract: A 2,2-difluoro-2-desoxycarbohydrate is used to prepare antiviral nucleosides.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: July 2, 1985
    Assignee: Eli Lilly and Company
    Inventor: Larry W. Hertel
  • Patent number: 4523020
    Abstract: This invention relates to novel substituted 2-(3-aminophenoxymethyl)imidazolines which are useful for the treatment of diarrhea and useful as analgesics.
    Type: Grant
    Filed: November 10, 1983
    Date of Patent: June 11, 1985
    Assignee: G. D. Searle & Co.
    Inventors: Alan E. Moormann, Barnett S. Pitzele, Peter H. Jones
  • Patent number: 4500720
    Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the production of numerous ester having elevated insecticidal activity.
    Type: Grant
    Filed: January 19, 1984
    Date of Patent: February 19, 1985
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4487957
    Abstract: A novel alkyl 4-methyl-3-formyl-penten-1-oate of the formula ##STR1## wherein R is alkyl of 1 to 5 carbon atoms and the dotted lines represent a double bond in the 3,4 or 4,5-position and their preparation and novel intermediates therefore and a novel process for the preparation of 4-methyl-3-formyl-pent-3-en-1-oic acid which is an intermediate for the preparation of compounds of the formula ##STR2## wherein R.sub.3 is selected from the group consisting of hydrogen and the residue of an alcohol R.sub.3 OH by the process of European Patent Application Ser. No. 0023849 published Feb. 11, 1981, which are used to prepare very active insecticidal esters.
    Type: Grant
    Filed: April 21, 1983
    Date of Patent: December 11, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4443617
    Abstract: Novel 3-formyl-4-methyl-pent-3-ene-1-oic acid of the formula ##STR1## and a process for its preparation and intermediates and a process for the preparation of compounds of the formula ##STR2## wherein W is selected from the group consisting of hydrogen and R.sub.1 of an optionally chiral alcohol R.sub.1 OH, useful as an intermediate for the producton of numerous ester having elevated insecticidal activity.
    Type: Grant
    Filed: July 1, 1982
    Date of Patent: April 17, 1984
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4443471
    Abstract: Novel ether, ester, urethane, thiourethane and carbonate derivatives of the ruminant growth promoters, M.139,603, M.139,603-adlehyde and oxime etc. derivatives thereof, all of which are effective in reducing the proportion of methane produced by ruminal fermentation, and increasing the proportion of propionic acid at the expense of acetic acid in the rumen contents; together with processes for their manufacture, compositions containing them, and their use in increasing growth and/or feed efficiency in ruminant animals.
    Type: Grant
    Filed: June 21, 1982
    Date of Patent: April 17, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: David H. Davies, Michael J. Smithers
  • Patent number: 4428886
    Abstract: The instant invention provides a new and improved method of preparing .alpha.-hydroxycarbonyl compounds, particularly substituted cyclopent-2-en-2-ol-1-ones and substituted 3-hydroxy-2(5H)-furanones. The novel sequence involves a number of novel intermediates including substituted 2-cyanocyclopentanones, substituted 2-cyano-2-hydroxycyclopentanones, and 2-cyano-2-hydroxyvalero-.gamma.-lactones.
    Type: Grant
    Filed: July 30, 1981
    Date of Patent: January 31, 1984
    Assignee: Givaudan Corporation
    Inventors: Ulrich Huber, Hans-Jakob Wild
  • Patent number: 4421922
    Abstract: Process for the production of tetronic acid from 4-haloacetoacetic ester which begins by converting a 4-haloacetoacetic ester into the corresponding 4-benzyloxyacetoacetic ester. The 4-benzyl ester is then hydrogenolyzed into an intermediate product. The 4-hydroxyacetoacetic ester is converted by treatment with acid into tetronic acid. The 4-hydroxyacetoacetic ester can be isolated before conversion. The 4-benzyloxyacetoacetic ester can be produced by conversion of the 4-haloacetoacetic ester with a metal salt of benzyl alcohol. The hydrogenolysis can be carried out in the presence of an acid, whereby the 4-hydroxyacetoacetic ester forming in situ is rearranged directly into tetronic acid. The hydrogenolysis can be carried out under pressure in the presence of a hydrogenation catalyst.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: December 20, 1983
    Assignee: Lonza Ltd.
    Inventors: Raimund Miller, Leander Tenud
  • Patent number: 4414400
    Abstract: Process for the production of tetronic acid from 4-haloacetoacetic ester. The 4-haloacetoacetic ester is transformed into the corresponding 4-tertiary-butoxyacetoacetic ester and the latter is converted by cyclizing ether cleavage into tetronic acid. Preferably the cyclizing ether cleavage is carried out thermolytically at a temperature above 100.degree. C. or is carried out by treatment with an acid at a temperature of 0.degree. to 30.degree. C. Tertiary-butoxyacetoacetic acid ethyl ester is a new compound.
    Type: Grant
    Filed: June 14, 1982
    Date of Patent: November 8, 1983
    Assignee: Lonza Ltd.
    Inventors: Raimund Miller, Leander Tenud
  • Patent number: 4414017
    Abstract: Compounds of the formula ##STR1## wheren X.sup.1 is halo or trihalomethyl, X.sup.2 is hydrogen or halo, R.sup.1 is nitro or --OR.sup.3, R.sup.2 is hydrogen or --OR.sup.4, R.sup.3 ##STR2## R.sup.4 is ##STR3## and R is hydroxy, alkoxy, alkenoxy, alkynoxy, thiol, alkythio, alkenylthio, amino, mono- or di-substituted amino or OM, wherein M is a monovalent cation; R' and R" are hydrogen, alkyl, alkenyl, alkynyl or phenyl; and Y is oxygen, sulfur, or substituted or unsubstituted nitrogen, have herbicidal activity.
    Type: Grant
    Filed: May 27, 1980
    Date of Patent: November 8, 1983
    Assignee: Chevron Research Company
    Inventor: David C. K. Chan
  • Patent number: 4410744
    Abstract: 1,2,4-Butanetriol is produced by hydroformylation of a solution of glycidol and reduction of the hydroformylation reaction products.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: October 18, 1983
    Assignee: Thiokol Corporation
    Inventors: Carol J. Campbell, Jerald C. Hinshaw
  • Patent number: 4410711
    Abstract: A method for the synthesis of lepiochlorin, an antibiotic.
    Type: Grant
    Filed: June 29, 1981
    Date of Patent: October 18, 1983
    Assignee: The Reagents of the University of California
    Inventors: Trevor C. McMorris, John R. Donaubauer
  • Patent number: 4402971
    Abstract: At least one algae-produced, substantially pure chemical compound with biocidal activity has been isolated from a blue-green algal (Cyanobacteria) toxin, preferably Scytonema toxin. This biocide appears to be one of the first of its class, since very little is now known regarding algal toxins and any biocides (including any antibiotics) they may contain. A biocide of this invention has activity against harmful blue-green algae such as Anabaena and can be used as, among other things, an algicide with minimal undesirable effects upon the environment of use (e.g. lakes, streams, water supplies, swimming pools, etc.). An ether-soluble, nonsteroidal, anisole-containing biocide of this invention appears to have a molecular weight of 430 or 431, a melting point or range within the range of about 48.degree. to about 55.degree. C., and the empirical formula C.sub.23 H.sub.23 O.sub.6 Cl.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: September 6, 1983
    Assignee: H. B. Fuller Company
    Inventor: Kent R. Edwards
  • Patent number: 4390724
    Abstract: Novel 3-formyl-4-methyl-pentanoic acid derivatives of the formula ##STR1## wherein Y is an aromatic group, R.sub.2 and R.sub.3 are individually alkyl of 1 to 4 carbon atoms or taken together with the carbon atom to which they are attached form a carbon homocycle of 3 to 6 carbon atoms, the Rs are alkyl of 1 to 6 carbon atoms or together form a polymethylene of 2 to 3 carbon atoms and Z' is selected from the group consisting of --COOH and Z and Z is selected from the group consisting of cyano and --COOR.sub.1 wherein R.sub.1 is alkyl of 1 to 6 carbon atoms and their preparation which are useful for the preparation of 3-formyl-4-R.sub.2 R.sub.3 -but-3-ene-1-oic acid which is an intermediate for the preparation of a compound of the formula ##STR2## wherein R.sub.4 is hydrogen or the remainder of an alcohol of the formula R.sub.1 OH by the process of copending, commonly assigned U.S. patent application Ser. No. 153,338 filed May 27, 1980.
    Type: Grant
    Filed: April 16, 1982
    Date of Patent: June 28, 1983
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4351839
    Abstract: This invention relates to 2-aryl-2-1-H-azoyl-(alkyl)gamma-butyrolactone of the formula: ##STR1## wherein Z is optionally substituted aryl;R is hydrogen, alkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aralkyl;Azo is 1-H-imidiazoyl, 1-H-1,2,4-triazoyl or 4-H-1,2,4-triazoyl;n is zero or an integer from 1 to 5, and the agronomically acceptable acid addition salts and metal salt complexes thereof, methods for their preparation and their use as pesticides.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: September 28, 1982
    Assignee: Rohm and Haas Company
    Inventor: Hak-Foon Chan