Plural Double Bonds Between Ring Members Of The Hetero Ring Patents (Class 549/471)
  • Patent number: 4623737
    Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and analogues thereof, which have demonstrated antiatherosclerotic activity.
    Type: Grant
    Filed: December 7, 1984
    Date of Patent: November 18, 1986
    Assignee: The Upjohn Company
    Inventor: Ayako Yamashita
  • Patent number: 4609739
    Abstract: The present invention provides novel compositions of matter and processes for their preparation. More particularly, the present invention consists of novel chemical intermediates and associated processes for the preparation of khellin and other furochromone analogues, which have demonstrated antiatherosclerotic activity. These novel intermediates and processes can also be used for the preparation of benzofurans and benzothiophenes which inhibit the synthesis of leukotriene and/or lipoxygenase.
    Type: Grant
    Filed: November 6, 1984
    Date of Patent: September 2, 1986
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4581457
    Abstract: There are disclosed compounds of the formula ##STR1## wherein X is ##STR2## W is ##STR3## Y is ##STR4## n is 0-8; R.sup.1 is hydrogen, loweralkyl, loweralkoxy, lower alkanoyl, halo, trifluoromethyl, cyano or nitro;R.sup.2 is hydrogen or loweralkyl;and the pharmaceutically acceptable salts thereof, and their use in the treatment of leukotriene-mediated naso-bronchial obstructive airpassageway conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and in antithrombotic therapy.
    Type: Grant
    Filed: September 21, 1984
    Date of Patent: April 8, 1986
    Assignee: American Home Products Corporation
    Inventors: John H. Musser, Dennis M. Kubrak
  • Patent number: 4558143
    Abstract: A 4-oxo-4,5,6,7-tetrahydrobenzofuran derivative is prepared by reacting a 1,3-cyclohexanedione derivative with chloroacetaldehyde in the presence of a base while maintaining the reaction mixture at a pH of from 4 to 10, and treating the reaction mixture with an acid. The 4-oxo-4,5,6,7-tetrahydrobenzofuran derivatives are useful as an intermediate for synthesis of various kinds of drugs.
    Type: Grant
    Filed: August 4, 1983
    Date of Patent: December 10, 1985
    Assignee: Sagami Chemical Research Center
    Inventors: Masakatsu Matsumoto, Nobuko Watanabe
  • Patent number: 4546177
    Abstract: The present invention provides novel 1-(6-hydroxy-4- or 7-methoxy or 4,7-dimethoxy-5-benzofuranyl)-4-substituted-1,3-butanediones which are useful as intermediates in the synthesis of khellin and related anti-atherosclerotic furochromones.
    Type: Grant
    Filed: April 24, 1984
    Date of Patent: October 8, 1985
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4537903
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: August 27, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
  • Patent number: 4535086
    Abstract: Heterocyclic compounds of the formula ##STR1## wherein X is --CH.dbd.CH--, --O-- or --S--; R.sup.1 is a group Ar--R.sup.2 or --CH.dbd.CH--C(CH.sub.3).dbd.CH--R.sup.21 ; Ar is phenyl, pyridyl, furyl or thienyl; R.sup.2 is a group --CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3, lower-alkylsulphonyl or formyl; R.sup.21 is a group--CO.sub.2 R.sup.3, --C(O)R.sup.4, --CH.sub.2 OR.sup.3 or formyl; R.sup.3 is hydrogen or lower-alkyl and R.sup.4 is hydrogen, hydroxy, amino, lower alkylamino, di-(lower alkyl)amino or lower-alkyl; at least one ring of the molecule being heterocyclic, salts thereof, processes for their preparation, rodenticidal compositions containing these compounds as the active ingredient and methods of use of the rodenticidal compositions are disclosed.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: August 13, 1985
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Michael Klaus, Peter Loeliger, Harald Weiser
  • Patent number: 4532340
    Abstract: The present invention provides novel intermediates used for preparation of anti-atherosclerotic furochromones.
    Type: Grant
    Filed: October 27, 1983
    Date of Patent: July 30, 1985
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4529721
    Abstract: A compound of the formula: ##STR1## wherein u represents hydrogen, carboxamido, N-hydroxycarboxamido, carboxy, azido, an aryl, an acylamino, a protected carboxy or an N-alkoxycarboxamido, or, together with v, can represent --S-- or --CH.sub.2 S--; v represents hydrogen, halogen, cyano or an alkylthio, or, together with u, can represent --S-- or --CH.sub.2 S--, or, together with w, can represent --(CH.sub.2).sub.3 CO--; w represents hydrogen, carboamoyl, cyano, carboxy, an N-alkylcarbamoyl, an alkyl, an aryl, a protected carboxy or a heterocycle, or, together with v, can represents --(CH.sub.2).sub.
    Type: Grant
    Filed: September 21, 1983
    Date of Patent: July 16, 1985
    Assignee: Shionogi & Co., Ltd.
    Inventors: Wataru Nagata, Mitsuru Yoshioka, Yasuhiro Nishitani, Tsutomu Aoki, Toshiro Konoike, Tadatoshi Kubota
  • Patent number: 4463185
    Abstract: The present invention provides novel 1-(6-hydroxy-4- or 7-methoxy or 4,7-dimethoxy-5-benzofuranyl)-4-substituted-1,3-butanediones which are useful as intermediates in the synthesis of khellin and related anti-atherosclerotic furochromones.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: July 31, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4459420
    Abstract: The present invention provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof from pyrogallol. Pyrogallol is converted to 3,6,7-benzofurantriol triacetate using zinc chloride and chloracetanitrile, then catalytically reduced and deactoxylated at the 3 position to yield the corresponding 2,3-dihydrofuran. This substance is subjected to a Fries rearrangement to the corresponding diol, the phenolic hydroxyl group of which is then selectively alkylated. This yields 6-hydroxy-7-alkoxy-5-benzofuranyl methyl ketone, a known intermediate for the production of 4-desmethoxy khellin and analogs thereof. This compound is then selectively alkoxylated at the 4 position using lead tetraacetate or thallium (III) nitrate in an alkanol solvent to yield known chemical intermediates in the preparation of khellin and analogs thereof.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: July 10, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4434296
    Abstract: The present specification provides a total synthesis of known intermediates useful in the synthesis of khellin and antiatherosclerotic analogs thereof. 3-Furoic acid is treated with succinic anhydride and diesterified to 3-carboxy-.delta.-oxo-2-furanbutanoic acid bis (alkyl ester). Following amination, cyclization and bis methylation, 6-formyl-4,7-dimethoxy-5-benzofurancarboxcyclic acid alkyl ester is prepared. This compound is then converted to known intermediates in the synthesis of khellin and analogs. Further, the present invention provides numerous novel anti-atherosclerotic 4,9-di-(C.sub.2 -C.sub.4)-alkoxyfurochromones.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: February 28, 1984
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4431650
    Abstract: This invention relates to novel esters of benzofuranyl acids, novel intermediates therefor, synthesis thereof, and the control of pests.
    Type: Grant
    Filed: December 22, 1980
    Date of Patent: February 14, 1984
    Assignee: Union Carbide Corporation
    Inventor: Thomas N. Wheeler
  • Patent number: 4424231
    Abstract: There are described compounds of formula I, ##STR1## in which Ra, Rb, Rc, Rd, Re, Rf and Rg, which may be the same or different, each represent hydrogen, amino, hydroxy, alkoxy, alkenyloxy, halogen, acyl, alkenyl, alkyl, or alkoxy substituted by phenyl,Rh is hydrogen, alkyl or --COOH.X is a hydrocarbon chain containing from 2 to 10 carbon atoms and optionally substituted by a hydroxy group,A has no significance or represents Y, OY, or SY and Y represents a C 1 to 4 hydrocarbon chain which is optionally substituted by alkyl C 1 to 4,E and G, which may be the same or different, each represent --O--, --S-- or --CH.sub.2 --, provided that at least one of E and G is --O-- or --S--,L, together with the carbon atoms to which it is attached, forms a benzene, furan, thiophene, pyrrole, or pyran-2-one ring,and pharmaceutically acceptable derivatives thereof.
    Type: Grant
    Filed: March 19, 1982
    Date of Patent: January 3, 1984
    Assignee: Fisons Limited
    Inventors: John R. Bantick, John Fuher, David N. Hardern, Thomas B. Lee
  • Patent number: 4412071
    Abstract: The present invention provides novel antiatherosclerotic furobenzoxazinones, e.g., 4,9-dimethoxy-4H-furo[3,2-g][1,3]benzoxazin-4-ones. These compounds are structurally and pharmacologically related to khellin and are useful antiatherosclerotic agents.
    Type: Grant
    Filed: May 17, 1982
    Date of Patent: October 25, 1983
    Assignee: The Upjohn Company
    Inventor: Ronald B. Gammill
  • Patent number: 4402968
    Abstract: Imidazole compounds of the formula ##STR1## wherein A is a group of the formula ##STR2## and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or a halogen atom,pharmaceutically acceptable acid addition salts thereof, pharmaceutical compositions containing these compounds are described. The compounds of formula I are useful as antifungal agents. Processes for preparing the novel compounds are also disclosed.
    Type: Grant
    Filed: May 29, 1981
    Date of Patent: September 6, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Joseph A. Martin
  • Patent number: 4372970
    Abstract: There are provided benzofuran-substituted acetic acid esters and compositions thereof having arthropocidal activity.
    Type: Grant
    Filed: July 9, 1981
    Date of Patent: February 8, 1983
    Assignee: Shell Internationale Research Maatschappij B.V.
    Inventors: Malcolm R. Hadler, David R. Woodward, Andrew A. Godfrey
  • Patent number: 4355168
    Abstract: There is disclosed and claimed a process for preparing aryl- and heteroarylhexadienoic acids which is characterized in that an aryl- or heteroarylacetylene having the formula: R--C.tbd.CH, wherein R is an aryl or heteroaryl group, optionally substituted and having in the aggregate up to 20 carbon atoms, is reacted with 3-butenoic acid CH.sub.2 .dbd.CH--CH.sub.2 --COOH, in an alcoholic medium, at temperatures maintained between 50.degree. C. and 120.degree. C., approximately, in the presence of a catalyst selected from among the phosphinic complexes of rhodium having the formulas: III, Rh(PR'.sub.3).sub.n L.sub.m X associated with alkaline salts of carboxylic acids having up to 4 carbon atoms, and IV, Rh(PR'.sub.3).sub.n L.sub.p.sup.+ Y.sup.
    Type: Grant
    Filed: December 2, 1980
    Date of Patent: October 19, 1982
    Assignee: Montedison S.p.A.
    Inventors: Gian P. Chiusoli, William Giroldini, Luciano Pallini, Giuseppe Salerno
  • Patent number: 4341792
    Abstract: Heterobicyclic glyoxylic acids, L- and DL-heterobicyclic glycines and their derivatives of the formulae ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein R is OR.sup.2 or NHR.sup.3 ;R.sup.2 is hydrogen or alkyl having from one to four carbon atoms;R.sup.3 is hydrogen, alkyl having from one to four carbon atoms, alkoxyalkyl having from one to four carbon atoms in each of the alkyl groups or R.sup.4 R.sup.5 C.sub.6 H.sub.3 CH.sub.2 -- where R.sup.4 and R.sup.5 are H, OH, F, Cl, Br, I, or alkyl or alkoxy having from one to four carbon atomsR.sup.1 is hydrogen, alkyl having from one to four carbon atoms or R.sup.4 R.sup.5 C.sub.6 H.sub.3 --; X is oxygen or sulfur; n is 0 or 1 and the broken line represents an optionally present double bond; useful in treatment of diseases and conditions which are characterized by reduced blood flow, reduced oxygen availability or reduced carbohydrate metabolism in the cardiovascular system.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 27, 1982
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, Peter E. Cross
  • Patent number: 4328169
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of an alkylene oxide derivative and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.
    Type: Grant
    Filed: October 27, 1980
    Date of Patent: May 4, 1982
    Assignee: Emery Industries, Inc.
    Inventor: Allen L. Hall
  • Patent number: 4328168
    Abstract: This invention provides a convenient and commercially adaptable process for the preparation of vinylcyclopropane derivatives in high yield. For the process an alkylating agent and activated methylene compound are reacted in the presence of a cyclic polyether compound and alkali metal compound. Water can also be present and/or the reaction may be carried out in an inert organic diluent.
    Type: Grant
    Filed: October 27, 1980
    Date of Patent: May 4, 1982
    Assignee: Emery Industries, Inc.
    Inventor: Richard G. Fayter, Jr.